Studies on the synthesis of apoptolidin: synthesis of a C1-C27 fragment of apoptolidin D

Madduri Srinivasarao; Youngsoon Kim; Xiaojin Harry Li; Daniel W Robbins; Philip L Fuchs

doi:10.1021/jo200934w

Studies on the synthesis of apoptolidin: synthesis of a C1-C27 fragment of apoptolidin D

J Org Chem. 2011 Oct 7;76(19):7834-41. doi: 10.1021/jo200934w. Epub 2011 Aug 26.

Authors

Madduri Srinivasarao¹, Youngsoon Kim, Xiaojin Harry Li, Daniel W Robbins, Philip L Fuchs

Affiliation

¹ Department of Chemistry, Purdue University, West Lafayette, Indiana 47907, United States.

PMID: 21827193
DOI: 10.1021/jo200934w

Abstract

Synthesis of a C(1)-C(27) fragment, a key intermediate in the synthesis of apoptolidin D, is reported. The synthesis involves a combination of Heck coupling and Horner-Wadsworth-Emmons reaction for the C(1)-C(7) trienoate portion and an efficient Suzuki cross-coupling protocol for the C(10)-C(13) diene portion.

MeSH terms

Alkenes / chemistry
Chemistry Techniques, Synthetic / methods*
Macrolides / chemical synthesis*
Macrolides / chemistry*

Substances

Alkenes
Macrolides
apoptolidin D