Oxocarbenium ion cyclizations for C-branched cyclitols: synthesis of a relay intermediate for fumagillin analogues.
A highly stereoselective oxocarbenium ion-alkene cyclization for synthesis of C-branched cylitols is described. This methodology was applied to 10S, a potentially versatile intermediate for side-chain analogues of the antiangiogenic agent fumagillin. Compound 10S was subsequently converted to diene 5. Because racemic 5 has been converted to racemic fumagillin, this synthesis of 5 constitutes a formal synthesis of the natural product.
Camara
Fatoumata
F
Department of Chemistry, Hunter College, 695 Park Avenue, New York, NY 10021, USA.
Angarita
Johana
J
Mootoo
David R
DR
D003500:Cyclization; D003510:Cyclohexanes; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D012717:Sesquiterpenes; D021241:Spectrometry, Mass, Electrospray Ionization
D003510:Cyclohexanes; D005231:Fatty Acids, Unsaturated; D012717:Sesquiterpenes; C026211:fumagillin