A new, ring closing metathesis-based synthesis of (-)-fumagillol.
[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.
Boiteau
J G
JG
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.
Van de Weghe
P
P
Eustache
J
J
D020533:Angiogenesis Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D003510:Cyclohexanes; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry
D020533:Angiogenesis Inhibitors; D003510:Cyclohexanes; D012717:Sesquiterpenes; C057299:fumagillol