Total synthesis of (+)-phomopsolide C by ring-size selective ring-closing metathesis/cross-metathesis

Simon Michaelis; Siegfried Blechert

doi:10.1021/ol052332k

Total synthesis of (+)-phomopsolide C by ring-size selective ring-closing metathesis/cross-metathesis

Org Lett. 2005 Nov 24;7(24):5513-6. doi: 10.1021/ol052332k.

Authors

Simon Michaelis¹, Siegfried Blechert

Affiliation

¹ Institut für Chemie, Technische Universität Berlin, Strasse des 17.Juni 135, 10623 Berlin, Germany.

PMID: 16288544
DOI: 10.1021/ol052332k

Abstract

[reaction: see text]A new strategy for the synthesis of chiral 6-substituted 5,6-dihydro-5-hydroxypyran-2-ones by ring-size selective ring-closing metathesis (RCM) and its application to a short total synthesis of (+)-phomopsolide C are described. The key bond-forming reactions in this approach are a chemoselective cross-metathesis (CM) and RCM.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cyclization
Molecular Structure
Pyrones / chemical synthesis*
Pyrones / chemistry
Stereoisomerism

Substances

Pyrones
phomopsolide C