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J Org Chem
; 70(17): 6870-5, 2005 Aug 19.
Article
in English
| MEDLINE
| ID: mdl-16095307
ABSTRACT
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.