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Total synthesis of (-)-spinosyn A
Dustin J Mergott1, Scott A Frank, William R Roush
1Department of Chemistry, University of Michigan, Ann Arbor, MI 48109, USA.
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.