Total synthesis of halichondrin C

Akihiko Yamamoto; Atsushi Ueda; Paul Brémond; Paolo S Tiseni; Yoshito Kishi

doi:10.1021/ja2108307

Total synthesis of halichondrin C

J Am Chem Soc. 2012 Jan 18;134(2):893-6. doi: 10.1021/ja2108307. Epub 2011 Dec 23.

Authors

Akihiko Yamamoto¹, Atsushi Ueda, Paul Brémond, Paolo S Tiseni, Yoshito Kishi

Affiliation

¹ Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.

PMID: 22188422
DOI: 10.1021/ja2108307

Abstract

The first total synthesis of halichondrin C has been completed, highlighted by development of the synthetic method to construct the C8-C14 polycycle. Cr-mediated coupling reactions are used seven times to form a new C-C bond. The acid stability of halichondrin C is studied, demonstrating that the macrolactone stabilizes the C8-C14 polycycle, relative to the one present in the C1-C16 model.

Publication types

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

MeSH terms

Animals
Ethers, Cyclic / chemical synthesis*
Macrolides / chemical synthesis*
Molecular Structure
Porifera

Substances

Ethers, Cyclic
Macrolides
halichondrin C