Total synthesis of (-)-spinosyn A.
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.
Mergott
Dustin J
DJ
Department of Chemistry, University of Michigan, Ann Arbor, MI 48109, USA.
Frank
Scott A
SA
Roush
William R
WR
D002625:Chemistry, Organic / Q000379:methods; D007306:Insecticides / Q000138:chemical synthesis / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D007306:Insecticides; D018942:Macrolides; C114883:spinosyn A