Synthesis of (+)-Cladospolide C

Chun-Yi Chou; Duen-Ren Hou

doi:10.1021/jo061767y

Synthesis of (+)-Cladospolide C

J Org Chem. 2006 Dec 22;71(26):9887-90. doi: 10.1021/jo061767y.

Authors

Chun-Yi Chou¹, Duen-Ren Hou

Affiliation

¹ Department of Chemistry, National Central University, Jung-Li City, Taoyuan, Taiwan 320.

PMID: 17168616
DOI: 10.1021/jo061767y

Abstract

(+)-Cladospolide C was synthesized in eight steps with 5% total yield, using methyl acrylate, (3R,4R)-1,5-hexadiene-3,4-diol, and (6R)-6-hepten-2-ol as the starting materials. Two cross-metathesis reactions and Yamaguchi esterification were applied to assemble the three units into (+)-Cladospolide C. Unsuccessful routes using ring-closing metathesis are also discussed.

Publication types

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

MeSH terms

Acrylates / chemistry
Macrolides / chemical synthesis*
Macrolides / chemistry
Molecular Conformation
Stereoisomerism

Substances

Acrylates
Macrolides
cladospolide C
methyl acrylate