Journal of Organic Chemistry p. 3658 - 3662 (1988)
Update date:2022-08-04
Topics:
Grieco, Paul A.
Parker, David T.
A total synthesis of (-)-8a-epipumiliotoxin C has been developed which features an intramolecular immonium ion based Diels-Alder reaction.Cyclocondensation of the immonium ion 8 derived from optically pure aldehyde 2 and ammonium chloride provided two octahydroquinolines 9 and 10, in a ratio of 2.2:1.The formation of 9 and 10 is rationalized on the basis of the chair-like conformations 16 and 17 respectively.Reduction of the double bond in 9 affored (-)-8a-epipumiliotoxin C.
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