Total synthesis of (-)-spinosyn A.

ABSTRACT: A convergent, highly stereoselective total synthesis of (-)-spinosyn A (1) is described. Key features of the synthesis include the transannular Diels-Alder reaction of macrocyclic pentaene 11 and the transannular Morita-Baylis-Hillman cyclization of 12 that generates tetracycle 26. The total synthesis of (-)-spinosyn A was completed by a sequence involving the highly beta-selective glycosidation reaction of 13 and glycosyl imidate 30.

SUBMITTER: Mergott DJ 

PROVIDER: S-EPMC514415 | biostudies-literature | 2004 Aug

REPOSITORIES: biostudies-literature