A General Strategy to Elisabethane Diterpenes:  Stereocontrolled Synthesis of Elisapterosin B via Oxidative Cyclization of an Elisabethin Precursor

Described is an efficient synthesis of the complex bioactive natural product, elisapterosin B, a potent in vitro inhibitor of Mycobacterium tuberculosis H37Rb. The synthesis elisapterosin B, prepared in its enantiomeric form, proceeds by a highly stereocontrolled sequence commencing with a simple gl...

Full description

Saved in:
Bibliographic Details
Published in:Journal of the American Chemical Society 2003-10, Vol.125 (43), p.13022-13023
Main Authors: Waizumi, Nobuaki, Stankovic, Ana R, Rawal, Viresh H
Format: Article
Language:English
Subjects:
Alicyclic compounds, terpenoids, prostaglandins, steroids
Anthozoa - chemistry
Chemistry
Cyclization
Diterpenes - chemical synthesis
Diterpenes - chemistry
Exact sciences and technology
Organic chemistry
Oxidation-Reduction
Preparations and properties
Stereoisomerism
Terpenoids
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Described is an efficient synthesis of the complex bioactive natural product, elisapterosin B, a potent in vitro inhibitor of Mycobacterium tuberculosis H37Rb. The synthesis elisapterosin B, prepared in its enantiomeric form, proceeds by a highly stereocontrolled sequence commencing with a simple glutamic acid derived compound. Pivotal steps in the sequence include (a) a pinacol-type ketal rearrangement to transfer chirality, (b) an IMDA reaction of an E,Z-diene to construct the elisabethin skeleton, and (c) a biosynthesis-inspired oxidative cyclization of the elisabethin precursor to elisapterosin B.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja035898h