A new, ring closing metathesis-based synthesis of (-)-fumagillol

J G Boiteau; P Van de Weghe; J Eustache

doi:10.1021/ol016343z

A new, ring closing metathesis-based synthesis of (-)-fumagillol

Org Lett. 2001 Aug 23;3(17):2737-40. doi: 10.1021/ol016343z.

Authors

J G Boiteau¹, P Van de Weghe, J Eustache

Affiliation

¹ Laboratoire de Chimie Organique et Bioorganique associé au CNRS, Université de Haute-Alsace, Ecole Nationale Supérieure de Chimie de Mulhouse, 3, Rue Alfred Werner, F-68093 Mulhouse Cedex, France.

PMID: 11506622
DOI: 10.1021/ol016343z

Abstract

[reaction: see text]. A new strategy to access the fumagillin/fumagillol skeleton is proposed. An Evans aldolization and a RCM involving an enone are used for the preparation of a key cyclohexanone intermediate, which was readily converted to fumagillol. The synthesis also features an efficient preparation of isogeraniol and isogeranic acid.

Publication types

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

MeSH terms

Angiogenesis Inhibitors / chemical synthesis*
Angiogenesis Inhibitors / chemistry
Cyclohexanes
Sesquiterpenes / chemical synthesis*
Sesquiterpenes / chemistry

Substances

Angiogenesis Inhibitors
Cyclohexanes
Sesquiterpenes
fumagillol