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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

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Total synthesis of (-)-spinosyn A.

Mergott Dustin J DJ Frank Scott A SA Roush William R WR

Proceedings of the National Academy of Sciences of the United States of America 20040601 33

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. ...[more]

PMID: 15173590

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