Jump to main content
Jump to site search

Issue 13, 2005
Previous Article Next Article

The stereocontrolled total synthesis of altohyrtin A/spongistatin 1: the southern hemisphere EF segment

Author affiliations

Abstract

The fully functionalised C29–C51 southern hemisphere of altohyrtin A/spongistatin 1 (1), incorporating the E- and F-ring tetrahydropyran rings and the unsaturated side chain, has been synthesised in a highly convergent and stereocontrolled manner. Key steps in the synthesis of this phosphonium salt include four highly diastereoselective, substrate-controlled, boron aldol reactions to establish key C–C bonds and accompanying stereocentres, where the introduction of the chlorodiene side chain and the C47 hydroxyl-bearing centre were realised by exploiting remote stereoinduction from the F-ring tetrahydropyran.

Graphical abstract: The stereocontrolled total synthesis of altohyrtin A/spongistatin 1: the southern hemisphere EF segment

Back to tab navigation

Supplementary files

Article information


Submitted
22 Mar 2005
Accepted
03 May 2005
First published
24 May 2005

Org. Biomol. Chem., 2005,3, 2420-2430
Article type
Paper

The stereocontrolled total synthesis of altohyrtin A/spongistatin 1: the southern hemisphere EF segment

I. Paterson, M. J. Coster, D. Y.-K. Chen, J. L. Aceña, J. Bach, L. E. Keown and T. Trieselmann, Org. Biomol. Chem., 2005, 3, 2420
DOI: 10.1039/B504149J

Social activity

Search articles by author

Spotlight

Advertisements