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.
Facile access to evodiakine enabled by aerobic copper-catalyzed oxidative rearrangement
Oxidative rearrangement for the first rapid construction of evodiakine was developed.
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.
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.
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.
Synthesis of solandelactone F, constanolactone A and an advanced intermediate towards solandelactone E from a common synthetic intermediate
Propargylic/allylic sulfides, obtained using α-chloro sulfides, are utilized for 1,4-diol synthesis in an iterative manner to create carbinol stereocenters.
A divergent strategy to synthesize gabosines featuring a switchable two-way aldol cyclization
Mode-switchable aldol cyclization of a diketone precursor enables a novel collective synthesis of divergent gabosine-type carbasugars.
Total synthesis of spiromastilactone A
Spiromastilactone A is synthesized for the first time in 44% overall yield in eight synthetic steps, among which six are quantitative, and the 89 : 11 enantiomeric ratio (78% ee value) is in favour of the right enantiomer (R configuration).
An efficient synthesis and bioactivity evaluation of oxazole-containing natural hinduchelins A–D and their derivatives
The efficient synthesis and bio-evaluation of hinduchelins A–D and their derivatives were investigated.
Asymmetric total synthesis of cryptoconcatone I
An efficient asymmetric total synthesis of naturally occurring γ-Z-butenolide cryptoconcatone I was achieved by employing substrate-directed reductive epoxide ring opening and late-stage “Pd–Cu” catalyzed cascade cyclization.
Improved synthesis of 2,4,6-trialkylpyridines from 1,5-diketoalkanes: the total synthesis of Anibamine
Many pyridine syntheses have been developed to date. In this study, we focused on pyridine synthesis with 1,5-diketone derivatives and hydroxylamine.
Total synthesis of levetiracetam
Total synthesis of levetiracetam via a one-pot dehydration/rearrangement of (R,E)-hept-4-en-3-ol carbamate to the corresponding allylamine derivative is reported.
Synthesis of resolvin E3 via palladium-catalyzed addition of AcOH to vinyl epoxy alcohols
(18R)- and (18S)-resolvins E3 were synthesized via the Pd-catalyzed addition of AcOH to the syn and anti isomers of vinyl epoxy alcohols.
Stereocontrolled synthesis of resolvin D1
Four pieces were assembled by the reactions indicated, and the dehydro precursor was semi-hydrogenated to give resolvin D1 (RvD1).
Total synthesis of (±)-galanthamine from GABA through regioselective aryne insertion
The total synthesis of (±)-galanthamine is achieved in ∼5% overall yield using a key regioselective aryne insertion reaction into a GABA (γ-amino butyric acid) derivative.
Synthesis and initial biological evaluation of myxocoumarin B
The first total synthesis of myxocoumarin B along with its initial biological evaluation in antifungal and cytotoxicity assays are reported.
Towards 20,20-difluorinated bryostatin: synthesis and biological evaluation of C17,C27-fragments
The syntheses of compounds corresponding to 20,20-difluorinated C17–C27 fragments of bryostatin are reported together with preliminary PKC binding data.
Solution-phase total synthesis of teixobactin
The first solution-phase total synthesis of teixobactin was completed with a 5.6% yield over 20 steps.
A novel approach to oxazole-containing diterpenoid synthesis from plant roots: salviamines E and F
Salviamines E and F were efficiently synthesized from a known molecule, 5,7,8-trimethoxy-1-naphthol.
Heterologous biosynthesis of a fungal macrocyclic polylactone requires only two iterative polyketide synthases
Formation of macrocyclic polylactone catalysed by only reducing and non-reducing polyketide synthases.
Synthesis of modified β-methoxyphenylalanines via diazonium chemistry and their incorporation in desoxycyclomarin analogues
Chloramphenicol base is converted into substituted syn-β-methoxyphenylalanins, building blocks of modified cyclomarins.
Cascade cyclization and intramolecular nitrone dipolar cycloaddition and formal synthesis of 19-hydroxyibogamine
Condensation of hydroxylamine and an aldehyde gave an azabicyclo[2.2.2]octane (isoquinuclidine) that was applied to a formal synthesis of 19-hydroxyibogamine.
Alkoxyallene-based syntheses of preussin and its analogs and their cytotoxicity
Preussin made in Prussia! Axially chiral alkoxyallenes provided oxa-preussin, racemic and enantiopure (−)-preussin (cytotoxicities: IC50 = 3–6 μM).
Bioactive spiropyrrolizidine oxindole alkaloid enantiomers from Isatis indigotica Fortune
Four pairs of new alkaloids, isatindigotindoline A–D, were isolated from Isatis indigotica, and were evaluated for their anti-Aβ1–42 aggregation effects.
A unified synthesis of topologically diverse Aspidosperma alkaloids through divergent iminium-trapping
Five Aspidosperma alkaloids within three structurally diverse topologies were synthesized from a single key intermediate, which could be selectively driven through three reaction paths: N(1)- vs. C(3)-indole cyclization vs. over-reduction, via the incorporation of conformational and electronic constraints that influence the reactivity of its derived iminium ion 7.
Four novel sesquiterpenoids with their anti-Alzheimer's disease activity from Nardostachys chinensis
Nardochinins A–D (1–4), four novel sesquiterpenoids, were isolated from Nardostachys chinensis. Nardochinin B (2) can significantly inhibit the Alzheimer's disease (AD) like symptom of worm paralysis.
Convergent total synthesis of (±) myricanol, a cyclic natural diarylheptanoid
Third total synthesis of the meta, meta-bridged diarylheptanoid: myricanol with remarkable anti-tau properties.
A synthetic study toward the core structure of (−)-apicularen A
A concise synthetic strategy towards the core structure of (−)-apicularen A has been described in an 11-step synthetic sequence from a known intermediate.
First enantioselective total synthesis of altersolanol A
The first enantioselective total synthesis of altersolanol A was accomplished by Diels–Alder cycloaddition promoted by (R)-3,3′-BINOL/boron Lewis acid.
Studies toward the synthesis of strevertenes A and G: stereoselective construction of C1–C19 segments of the molecules
Efficient route for the stereoselective synthesis of common C1–C19 segment of strevertenes A and G has been developed.
Synthesis of macrocyclic precursors of the vioprolides
Convergent syntheses have been developed of macrocycles that may be useful for the synthesis of vioprolide D. Preliminary studies have also been carried out into the introduction of the thiazoline and (E)-dehydrobutyrine components.
Toward the total synthesis of patellazole B: synthesis of an advanced C1–C25 fragment corresponding to the macrocyclic skeleton
A modular and highly convergent approach enables the assembly of an advanced intermediate towards the total synthesis of patellazole B – a promising anticancer agent.
Functionalization of diazotetronic acid and application in a stereoselective modular synthesis of pulvinone, aspulvinones A–E, G, Q and their analogues
Diastereoselective aldol condensation of diazotetronic acid and a subsequent arene C–H insertion provides an efficient route to the aspulvinone motif.
Enantioselective total synthesis of decytospolide A and decytospolide B using an Achmatowicz reaction
Enantioselective syntheses of decytospolides are described using an Achmatowicz rearrangement, transfer hydrogenation and Friedel–Crafts acylation as the key steps.
Enantioselective total synthesis and biological evaluation of (−)-solanacol
An enantioselective synthesis of the phenyl ring-containing strioglactone, (−)-solanocol, is described.
Total synthesis of the proposed structure of talarolide A
The proposed structure of talarolide A, a cycloheptapeptide featuring a hydroxamate moiety within the peptide backbone, was successfully synthesized.
Asymmetric total synthesis of naturally occurring spirocyclic tetranorsesquiterpenoid lanceolactone A
Asymmetric total synthesis of naturally occurring γ-butenolide containing [4.4]spiro-tetrahydrofuran lanceolactone A has been reported in this present work. Bimetallic (“Pd–Cu”) cascade cyclization was the crucial reaction employed for the construction of the γ-butenolide framework of the natural product.
Total synthesis and structural revision of an isopanepoxydone analog isolated from Lentinus strigellus
Asymmetric total synthesis of compound 1, as a proposed molecular structure of a natural product, in 11 steps is described. The inconsistency of the characterization data prompted us to propose a different structure as compound 2 and accordingly accomplish total synthesis in 9 steps and confirm the structural revision of this natural product.
Total synthesis and structural revision of (±)-nidemone
Total synthesis and structural revision of (±)-nidemone have been accomplished from 6-bromo-2-hydroxybenzaldehyde (5) in either six or eight synthetic steps.
Total synthesis of 1α,25-dihydroxyvitamin D3 analogs modified at the side chain and D-ring
A general approach to generate the natural or unnatural steroid configuration at C20 and unsaturation at the D-ring is exemplified with the total synthesis of 1α,25-dihydroxyvitamin D3 analogs 3 and 4.
About this collection
The latest articles published in Organic and Biomolecular Chemistry related to total synthesis.