Synthesis of the C7-26 fragment of amphidinolides G and H

Akihiro Hara; Ryo Morimoto; Yuichi Ishikawa; Shigeru Nishiyama

doi:10.1021/ol201547q

Synthesis of the C7-26 fragment of amphidinolides G and H

Org Lett. 2011 Aug 5;13(15):4036-9. doi: 10.1021/ol201547q. Epub 2011 Jul 11.

Authors

Akihiro Hara¹, Ryo Morimoto, Yuichi Ishikawa, Shigeru Nishiyama

Affiliation

¹ Department of Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi 3-14-1, Yokohama 223-8522, Japan.

PMID: 21744852
DOI: 10.1021/ol201547q

Abstract

A new approach to the synthesis of the C7-26 fragment of amphidinolides G and H was developed. In the sequence, the C7-18 portion of this fragment was synthesized using an acetylide coupling protocol, while an Evans alkylation and Sharpless asymmetric dihydroxylation were employed as key steps in construction of the C19-26 subfragment. Finally, both of these units were joined by utilizing an aldol coupling reaction to produce the target C7-26 fragment in good yield.

Publication types

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

MeSH terms

Alkylation
Macrolides / chemical synthesis*
Models, Molecular
Molecular Structure
Stereoisomerism

Substances

Macrolides
amphidinolide G
amphidinolide H