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The total synthesis and stereochemical revision of yanucamide A.

Abstract

[reaction: see text] The first total synthesis of yanucamide A is reported via amide and ester couplings of the key components. This synthesis has established the configuration at the previously ambiguous 3-position, and also revised the stereochemistry at the 22-position, to give 3S,12S,17S,22S for the natural product.

Entities: Chemical

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Year: 2003 PMID： 12889883 DOI： 10.1021/ol034803d

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

8 in total

1. Parallel synthesis of an oligomeric imidazole-4,5-dicarboxamide library.

Authors: Zhigang Xu; John C DiCesare; Paul W Baures
Journal: J Comb Chem Date: 2010-03-08

2. Expedient synthesis of α,α-dimethyl-β-hydroxy carbonyl scaffolds via Evans' aldol reaction with a tertiary enolate.

Authors: Joshawna K Nunnery; Takashi L Suyama; Roger G Linington; William H Gerwick
Journal: Tetrahedron Lett Date: 2011-06-08 Impact factor: 2.415

3. Viequeamide A, a cytotoxic member of the kulolide superfamily of cyclic depsipeptides from a marine button cyanobacterium.

Authors: Paul D Boudreau; Tara Byrum; Wei-Ting Liu; Pieter C Dorrestein; William H Gerwick
Journal: J Nat Prod Date: 2012-08-27 Impact factor: 4.050

The total synthesis and stereochemical revision of yanucamide A.

1. Parallel synthesis of an oligomeric imidazole-4,5-dicarboxamide library.

2. Expedient synthesis of α,α-dimethyl-β-hydroxy carbonyl scaffolds via Evans' aldol reaction with a tertiary enolate.

3. Viequeamide A, a cytotoxic member of the kulolide superfamily of cyclic depsipeptides from a marine button cyanobacterium.

4. Studies toward the total synthesis of Itralamide B and biological evaluation of its structural analogs.

5. Total synthesis of the putative structure of the proposed Banyasin A.

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8. Total Synthesis of the Highly N-Methylated Peptides Carmabin A and Dragomabin.