Stereoselective Syntheses of Epothilones A and B via Nitrile Oxide Cycloadditions and Related Studies

The expedient and fully stereocontrolled synthesis of epothilones A and B are described. The routes described make extensive study of nitrile oxide cycloadditions as surrogates for aldol addition reactions and have led to the realization of a highly convergent synthesis based on the Kanemasa hydroxy...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2001-09, Vol.66 (19), p.6410-6424
Main Authors: Bode, Jeffrey W, Carreira, Erick M
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Antineoplastic Agents - chemical synthesis
Cyclization
Epothilones
Epoxy Compounds - chemical synthesis
Molecular Conformation
Nitric Oxide - chemistry
Thiazoles - chemical synthesis
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:The expedient and fully stereocontrolled synthesis of epothilones A and B are described. The routes described make extensive study of nitrile oxide cycloadditions as surrogates for aldol addition reactions and have led to the realization of a highly convergent synthesis based on the Kanemasa hydroxyl-directed nitrile oxide cycloaddition. As well, our synthetic efforts have led to the development of new reaction methodologies and served as the proving ground for several modern methods for asymmetric carbon−carbon bond formation.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo015791h