Themed collection Natural product synthesis

The recent developments on the [5+2] cycloadditions and their application in the synthesis of complex natural products are discussed.

Radical translocation facilitates the regioselective γ-amination of 2-alkyl-substituted azacycles, leading to 1,3-diamines including the alkaloidal natural product tetraponerine T8.

A highly selective metal-free CDC approach for the synthesis of 1-indolyltetrahydro-β-carbolines is developed. The total synthesis of biologically important alkaloids, eudistomin U and isoeudistomin U and the first total synthesis of 19-bromoisoeudistomin U were accomplished.

The collective total synthesis of (+)-sinensilactam A, (+)-lingzhilactone B, (+)-lingzhilactone C and (−)-lingzhiol has been accomplished from a common epoxide intermediate 9.

The synthesis of di-O-methylendiandrin A has been achieved using diastereoselective, vicinal alkylation and transannular McMurry reactions of a macrocyclic 1,4-diketone, to establish stereochemistry and the strained ring of the natural product.

Flavoskyrins, (−)-rugulosin B, C and rugulin analogues are synthesized chemoenzymatically from anthraquinones in two, three and four steps, respectively.

Analysis of bound structures and SAR studies led to the function-oriented simplification of the aplyronines; a convergent and modular synthetic platform then enabled the total synthesis and biological evaluation of four novel analogues.

A facile and environmentally benign KI(cat.)/NaBO₃·4H₂O oxidation system has been developed for the tandem oxidative aminocyclization/coupling of tryptamines, affording a series of 3a,3a′-bispyrrolidino[2,3-b]indolines with high efficiency (up to 94% yield).

The first total synthesis of vercopeptin (1), an inhibitor of hypoxia-inducible factor 1 (HIF-1), was achieved via condensation of the depsipeptide core and the polyketide side chain unit.

This work describes the first total synthesis of mortiamides and their anti-malarial activity against a multi-drug resistant strain of Plasmodium falciparum.

The organocatalytic enantioselective Friedel–Crafts alkylation of the phloroglucinol derivatives with enals is reported, providing general access to the benzylic chiral centers shown in a variety of phloroglucinol natural products.

A synthetic approach to chrysophaentin F is described featuring an array of metal catalysed coupling reactions (Cu, Ni, Pd, W, Mo).

Transition metal catalyzed [2+2+2] cycloaddition and aromatic C–H oxygenation enables concise, divergent total syntheses of five bioactive illudalane sesquiterpenes.

The first asymmetric total synthesis of a member of the asperparaline family was accomplished and the unknown absolute configuration of asperparaline C has been determined to be all-(S).

A unified strategy enabled the enantioselective syntheses of (−)-scholarisine G, (+)-melodinine E, (−)-leuconoxine and (−)-mersicarpine from a common 2-alkylated indole bearing an all-carbon quaternary stereogenic center.

Efficient access to evodiamine and its analogues is presented via Lewis acid catalysis. In this reaction, three chemical bonds and two heterocyclic-fused rings are constructed in one step.

Here we report a total synthesis of the pharmacologically significant morphinan alkaloid, oxycodone.

An expedient route to the pentacyclic core of the tryptoquivaline alkaloids and the total synthesis of natural product (+)-3′-(4-oxoquinazolin-3-yl)spiro[1H-indole-3,5′-oxolane]-2,2′-dione (1) have been achieved.

The first asymmetric total synthesis of pleurospiroketals A and B has been accomplished in 16 steps from 5-methyl-5-hexenoic acid.

A new synthetic approach to (−)-agelastatin A has been established through the strategic implementation of brominative olefin transposition of a silyl enol ether and subsequent S_H2′ radical azidation of the resultant allylic bromide.

Benefiting from a highly diastereoselective alkylation of (S)-Taniguchi lactone, a double Friedel–Crafts reaction, a global debenzylation and a Cu(OAc)₂-enabled benzylic oxidative cyclization, an efficient synthetic approach to (+)-ovafolinins A and B has been developed.

The first enantioselective total synthesis of eremophilane-type sesquiterpenoids, sagittacin E and related natural products, was achieved.

Alkenyl bromide functionality survives several synthetic steps, including an acid-induced rearrangement, before a stereoretentive methylative debromination gives the natural product.

A concise, asymmetric and divergent synthesis of lycoposerramine R and lycopladine A is presented.

The asymmetric synthesis of an anti-cancer spirooxindole alkaloid, (−)-strychnofoline, has, for the first time, been accomplished in only nine steps.

The strategy developed for the first total synthesis of highly oxygenated natural product conosilane A involving double manipulation of allylic C(sp³)–H functionalization renders the power of C–H functionalization in organic syntheses.

Catalytic asymmetric formal syntheses of both enantiomers of (+)- and (−)-cycloclavine (1) have been envisioned via proline catalysed α-aminoxylation of aldehydes followed by an intramolecular Heck cyclization to set vicinal stereocenters.

The enantioselective total synthesis of (+)-brasilenyne, which has a unique oxonane framework containing a 1,3-cis,cis-diene, has been accomplished.