Total synthesis of (–)-spinosyn A

AUTOR(ES)

Mergott, Dustin J.

FONTE

National Academy of Sciences

RESUMO

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 β-selective glycosidation reaction of 13 and glycosyl imidate 30.

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