Emergence of 2,3,5-trisubstituted tetrahydrofuran natural products and their synthesis
Diverse syntheses of emerging 2,3,5-trisubstituted-THF natural products are reviewed encompassing strategies based on catalytic methods, cascade reactions and rearrangements.
Total synthesis of natural products using photocycloaddition reactions of arenes
The photocycloaddition reaction of benzene with alkenes has become a significant approach for organic chemists and thus has been frequently utilized as a key step in the total synthesis of natural products.
Strategies for the construction of γ-spirocyclic butenolides in natural product synthesis
This review describes the stereoselective synthesis of a γ-spirocyclic containing natural products or model compounds showing phytotoxic, antibiotic, anti-inflammatory, antiviral, antimicrobial, cytotoxic, and antitumor activities.
Palladium-catalyzed asymmetric dearomative cyclization in natural product synthesis
This review discusses palladium-catalyzed asymmetric dearomative cyclization, which is invaluable for producing enantioenriched materials, for complex natural product synthesis.
Synthetic approaches towards cortistatins: evolution and progress through its ages
With an exhaustive coverage of all the synthetic approaches towards cortistatins, this review serves to assemble most of the avenues which have been employed to conquer this complex steroidal alkaloid architecture.
Asymmetric copper-catalyzed conjugate additions of organometallic reagents in the syntheses of natural compounds and pharmaceuticals
Stereoselective copper-catalyzed conjugate additions of organometallic reagents serve as a versatile tool in the total syntheses of diverse natural compounds and pharmaceutical agents.
Synthetic pathways to tetrahydrocannabinol (THC): an overview
This review summarises various synthetic pathways leading to tetrahydrocannabinol and structurally related cannabinoids.
Recent progress in the total synthesis of Strychnos alkaloids
The recent synthetic approaches toward Strychnos alkaloids are summarized, including novel synthetic methodologies and strategies.
Recent progress in the total synthesis of marine brominated sesquiterpene aplydactone
In this review, we summarize five instructive total syntheses of marine brominated sesquiterpene aplydactone developed over the past five years.
Synthetic approaches towards avibactam and other diazabicyclooctane β-lactamase inhibitors
The synthetic strategies to obtain avibactam and other diazabicyclooctane β-lactamase inhibitors such as ETX2514 are presented.
Full solid-phase total synthesis of macrocyclic natural peptides using four-dimensionally orthogonal protective groups
This review focuses on four-dimensionally orthogonal protective group strategies for the full solid-phase synthesis of macrocyclic natural peptides.
Versatility of glycals in synthetic organic chemistry: coupling reactions, diversity oriented synthesis and natural product synthesis
Versatility of glycals in the stereoselective synthesis of natural products.
Progress in total synthesis of subincanadine alkaloids and their congeners
Total synthesis of subincanadine alkaloids and their biogenetic congeners are described in a focused manner.
Recent advances in the synthesis of azaphenalene alkaloids: first enantioselective approaches
This review provides an update of the synthetic progress towards azaphenalene alkaloids, including the pioneering enantioselective approaches.
Natural products as modulators of the cyclic-AMP pathway: evaluation and synthesis of lead compounds
Natural product modulators of the cAMP pathway have been evaluated and their total synthesis campaign is described in detail.
Review of synthetic approaches toward maoecrystal V
Synthetic approaches toward the complex natural product diterpenoid maoecrystal V are reviewed, including successful total syntheses, published synthetic efforts, and efforts compiled from dissertations.
Total synthesis of complex alkaloids by nucleophilic addition to amides
This mini review focuses on the recent progress of total synthesis of complex alkaloids based on the nucleophilic additions to N-alkoxyamides, tertiary amides and secondary amides.
Total synthesis of tubulysin U and N14-desacetoxytubulysin H
A concise and efficient procedure for the total synthesis of tubulysin U and N14-desacetoxytubulysin H has been developed with high stereoselectivity on a gram scale.
Stereoselective synthesis of an eleganine A core
The core structure of eleganine A – a cytotoxic indole monoterpene alkaloid – was accessed for the first time.
Synthesis of B-ring-fluorinated (−)-epicatechin gallate derivatives
Electronically modified, fluorinated catechins and epicatechins are enantioselectively synthesized in a short, convergent sequence via kinetic resolution.
Divergent syntheses of okaramines C, J, L, and S–U
The first total synthesis of okaramines L and S–U, and the concise synthesis of okaramines C and J have been accomplished using a common intermediate bromohexahydropyrroloindole in 5–8 steps with an overall yield of 6.7%–23.0%.
Total synthesis of tricolorin A via interrupted Pummerer reaction-mediated glycosylation and one-pot relay glycosylation
The total synthesis of tricolorin A was achieved with high efficiency based on interrupted Pummerer reaction-mediated (IPRm) glycosylation and one-pot relay glycosylation.
Total synthesis of isatindigotindoline C
Total synthesis of isatindigotindoline C is achieved in two steps using a biomimetic 1,3-dipolar cycloaddition reaction as the key step.
Syntheses of doubly linked proanthocyanidins using free flavan units as nucleophiles: insight into the origin of the high regioselectivity of annulation
Reported herein is a viable synthesis route to procyanidins A1 and A2, doubly linked flavan dimers. The use of nascent nucleophilic partner, catechin or epicatechin, enabled facile regioselective annulation with an ethylenedioxy-bridged flavan unit.
Facile access to evodiakine enabled by aerobic copper-catalyzed oxidative rearrangement
Oxidative rearrangement for the first rapid construction of evodiakine was developed.
Total syntheses of seminolipid and its analogues by using 2,6-bis(trifluoromethyl)phenylboronic acid as protective reagent
Total synthesis of seminolipid was accomplished via regioselective protection using 2,6-bis(trifluoromethyl)phenylboronic acid followed by regioselective trichloroethyl-protected sulfation as key steps.
Total synthesis of (+)-ar-macrocarpene
First total synthesis of a naturally occurring sesquiterpenoid, (+)-ar-macrocarpene, has been achieved via a key [3,3]-sigmatropic rearrangement effecting reductive transposition through allylic diazene rearrangement (ADR).
A biomimetic approach towards phorone sesterterpenoids
We report efforts towards a unified total synthesis of Korean sponge derived sesterterpenoids phorones A and B, using a biomimetic strategy. This work has established a new synthetic approach to the parent ansellane sesterterpenoid skeleton with unanticipated diversion along a biogenetically related pathway.
Total synthesis of (±)-epi-stemodan-13α,17-diol
Stemodan-13α,17-diol is a natural stemodane-type diterpenoid isolated from Stemodia chilensis.
A new route to tricyclane sesquiterpenoids: total synthesis of α-ekasantalic acid
Chemical manipulation of the cycloadduct of citraconic anhydride and cyclopentadiene enables a new synthetic route to tricyclane sesquiterpenoids.
Total synthesis of (±)-antroquinonol
We report the total synthesis of (±)-antroquinonol based on a concise and efficient route.
Palladium-catalyzed intramolecular carboborylation of 1,3-diene and synthesis of ABCD ring of communesins
A palladium-catalyzed intramolecular carboborylation of 1,3-diene has been developed for the synthesis of iminoindolines with a quaternary carbon centre.
Synthesis of the core structure of phalarine
Two new palladium-catalyzed reactions enabled the synthesis of the core structure of phalarine.
Total synthesis of incargranine A
Synthetic studies into the origins of the alkaloid incargranine A have resulted in the development of a four-step (longest linear sequence) total synthesis.
Synthesis and biological evaluation of fluorinated analogues of ripostatin A
A last stage click-chemistry approach to synthesize the heterocycle-containing derivatives of fluorinated ripostatin A was developed.
Enantioselective synthesis and absolute configuration determination of hydroxywilfordic acid in sesquiterpene pyridine alkaloids
An enantioselective synthetic route to hydroxywilfordic acid, a key subunit of sesquiterpene pyridine alkaloids such as wilfortrine, was developed.
Total synthesis of the potent anti-inflammatory natural product solomonamide A along with structural revision and biological activity evaluation
Herein, we report the total synthesis of solomonamide A along with its structural revision for the first time.
Syntheses of the plant auxin conjugate 2-O-(indole-3-acetyl)-myo-inositol IAInos
The two first chemical syntheses of IAInos (2-O-(indole-3-acetyl)-myo-inositol), an important plant hormone, are described.
Semi-syntheses of the 11-hydroxyrotenoids sumatrol and villosinol
We describe semi-syntheses of the 11-hydroxyrotenoids sumatrol (1) and villosinol (2), starting from rotenone (5), using an oxime-directed C11–H functionalisation approach.
Biomimetic total syntheses of chromane meroterpenoids, guadials B and C, guapsidial A and psiguajadial D
The first biomimetic total syntheses of chromane meroterpenoids, guadials B and C, guapsidial A and psiguajadial D have been completed.
Synthesis of two new gem-fluoronitro containing tetranitroadamantanes and property comparison with their nitro and gem-dinitro analogues
Two new fluorinated tetranitroadamantanes were synthesized and their physical properties were compared with their analogues on the basis of experimental and calculated results.
Synthesis of the [7-5-5] tricyclic core of Daphniphyllum alkaloids
The [7-5-5] tricyclic core of the Daphniphyllum alkaloids was constructed, featuring a Claisen-Ireland rearrangement to install the two contiguous stereogenic centers, E1cB elimination to form the tetrasubstituted C–C double bond, and a 2,3-Wittig rearrangement to construct the quaternary carbon.
Stereoselective preparation of key intermediates for the synthesis of iso-, neuro- and phyto-prostane family members: inaugural asymmetric synthesis of 17-E2c-dihomo- and 17-F2c-dihomo-isoprostanes
A practical synthesis of enantiopure key intermediates for the preparation of prostanoids has been described.
Concise total synthesis of (+)-asperazine A and (+)-pestalazine B
The highly convergent total synthesis of dimeric diketopiperazine alkaloids (+)-asperazine A and (+)-pestalazine B is described.
Synthesis and antiproliferative effect of the proposed stereoisomer of the marine sponge metabolite halisphingosine A
The purported isomer of halisphingosine A was built up in 11 steps and 29% yield by catalytic Henry and hydrogenation reactions. Its 13C-NMR data differed from that of the natural isolate. It was antiproliferative in various tumour cells.
Biselyngbyolides A & C: their total synthesis and anticancer activities
Convergent strategies have been developed for the total synthesis of biselyngbyolides A & C, and their anticancer activities were described.
A pyridinium anionic ring-opening reaction applied to the stereodivergent syntheses of Piperaceae natural products
Expanding the scope of a pyridinium ring-opening reaction, a practical oxidation protocol has been devised to access isomerically pure bromodiene esters. The utility is demonstrated in a divergent strategy to obtain two natural TRPV1 agonist motifs.
Route exploration and synthesis of the reported pyridone-based PDI inhibitor STK076545
A 5-step synthesis of a reported PDI inhibitor was developed using an aldol reaction with an allyl ester. Conventional approaches for preparing β-keto amides with a pyridone in the alpha position were complicated by undesired fragmentations or rearrangements.
Synthetic studies on palmerolide C: synthesis of an advanced intermediate towards the revised structure of palmerolide C
Herein, we describe the stereoselective synthesis of highly functionalized advanced key intermediates towards the total synthesis of the revised structure of palmerolide C and 10-epi-palmerolide C in a convergent manner.
Total synthesis and biological evaluation of seven new anti-inflammatory oxacyclododecindione-type macrolactones
Seven new macrolactones of the oxacyclododecindione family have been synthesized and tested for their inhibitory activity on TGF-β-inducible Smad2/3- as well as IL-4-inducible STAT6-dependent signalling pathways.
An efficient approach for the synthesis of new (±)-coixspirolactams
An easy access to (±)-coixspirolactam A and a large number of new coixspirolactams was developed.
Total synthesis of four stereoisomers of methyl 4,8,12-trimethylpentadecanoate, a major component of the sex pheromone of the stink bug Edessa meditabunda
A convergent synthetic route was developed for the stereoselective synthesis of four stereoisomers of methyl 4,8,12-trimethylpentadecanoate. The Fouquet-Schlosser variant of the Grignard reaction was used as key steps.
Synthesis of proteasome inhibitor 6-deoxy-omuralide and its enantiomer using stereoselective alkylation of substituted proline ester
A potent 20S proteasome inhibitor, 6-deoxy-omuralide 28, and its enantiomer of 29 were synthesized using stereoselective alkylation of the corresponding substituted proline esters as the key step.
Improved total synthesis of the antibiotic A54145B
An optimized synthetic route of the antibiotic A54145B has been developed in terms of the overall yield and time required.
Asymmetric synthesis of (−)-solanidine and (−)-tomatidenol
The asymmetric synthesis of (−)-solanidine (1) and (−)-tomatidenol (2) has been achieved by employing a cascade ringswitching reaction and a cascade azide reduction/intramolecular reductive amination with 32% and 18.7% overall yields respectively.
A modular approach to the bisbenzylisoquinoline alkaloids tetrandrine and isotetrandrine
A modular short-step synthesis of the bisbenzylisoquinoline alkaloids tetrandrine and isotetrandrine was developed employing N-acyl-Pictet–Spengler reaction and Ullman diaryl ether synthesis as central steps.
An alternative approach to the synthesis of the three fragments of anachelin H
The synthesis of the fully protected peptide, polyketide and alkaloid fragments of anachelin H is presented, using an alternative approach to previously reported synthesis and based on naturally occurring amino acids as sources of asymmetry.
Construction of key building blocks towards the synthesis of cortistatins
This work reports the construction of key building blocks towards the synthesis of cortistatins; a family of steroidal alkaloids. D-glucose and Hajos–Parrish ketone were employed as chiral pools for the A-ring and DE-ring fragments respectively.
Asymmetric total syntheses of naturally occurring α,β-enone-containing RALs, L-783290 and L-783277 through intramolecular base-mediated macrolactonization reaction
Asymmetric total synthesis of two naturally occurring α,β-enone containing RALs, L-783290 and L-783277 is described in this article.
Total synthesis of nafuredin B
Asymmetric total synthesis of nafuredin B has been achieved for the first time following a convergent approach.
Formal enantioselective synthesis of nhatrangin A
A new and straightforward synthesis of the C1–C7 core fragment of nhatrangin A was achieved in 14 steps from achiral 3-hydroxybenzaldehyde, without the need of chiral reagents or enzymatic resolution to introduce the chiral centers.
Total synthesis of exigurin: the Ugi reaction in a hypothetical biosynthesis of natural products
Bioinspired U-5C-4CR employing (−)-10-epi-axisonitrile-3, formaldehyde and sarcosine in methanol showed remarkable efficiency to assemble multicomponents in a one-pot process, leading to the first total synthesis of exigurin.
Studies toward the synthesis of macrotermycin C: stereoselective construction of the acyclic skeleton of the aglycon
The first asymmetric synthesis of the acyclic skeleton of the aglycon of macrotermycin C has been achieved in 17 linear steps with 5.7% overall yield following a convergent approach.
Total synthesis of wikstrol A and wikstrol B
The first total synthesis of wikstrol A and wikstrol B was achieved via Sharpless asymmetric dihydroxylation, Sonogashira and rhodium-catalyzed oxidative coupling as key steps.
Bio-inspired enantioselective total syntheses of (−)-viminalins A, B, H, I, and N and structural reassignment of (−)-viminalin M
Bio-inspired enantioselective total syntheses of (−)-viminalins A, B, H, I, and N, isolated from the Myrtaceae family, were accomplished in a convergent fashion in 5, 5, 1, 1, and 3 steps, respectively.
Asymmetric total synthesis of paecilomycin C through intramolecular nucleophilic ring opening of an epoxide
An efficient asymmetric total synthesis of naturally occurring resorcylic acid lactone (RAL) paecilomycin C was achieved by employing carboxylate assisted 5-exo-tet ring opening of an epoxide as a key reaction.
Unified synthesis and cytotoxic activity of 8-O-methylfusarubin and its analogues
A unified total synthesis of 8-O-methylfusarubin, 8-O-methylanhydrofusarubin, fusarubin and anhydrofusarubin and their cytotoxic activities against six cancer cell lines are described.
Total syntheses of several iridolactones and the putative structure of noriridoid scholarein A: an intramolecular Pauson–Khand reaction based one-stop synthetic solution
A general synthetic strategy featuring a diastereoselective intramolecular Pauson–Khand reaction (IPKR) and some tactical synthetic manoeuvres to access ten iridoids in a stereocontrolled manner is delineated.
Total syntheses of the bilirubin oxidation end product Z-BOX C and its isomeric form Z-BOX D
The bilirubin degradation product BOX C has been detected in human bile. The total synthesis of this biomolecule allows an extensive characterization including elucidation of its X-ray structure.
Total synthesis and stereochemical revision of relgro and 10′-oxorelgro
The first total synthesis and correct stereochemical assignments of relgro (6′S,10′S)-configuration and 10′-oxorelgro with (6′S)-configuration are described.
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The latest articles published in Organic and Biomolecular Chemistry related to total synthesis.