Daphniphyllum alkaloids. 10. Classical total synthesis of methyl homodaphniphyllate

CH Heathcock, SK Davidsen, SG Mills…

Index: Heathcock, Clayton H.; Davidsen, Steven K.; Mills, Sander G.; Sanner, Mark A. Journal of Organic Chemistry, 1992 , vol. 57, # 9 p. 2531 - 2544

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Citation Number: 89

Abstract

Details for the fist total synthesis of a Daphniphyllum alkaloid are presented. The synthesis required a total of 15 steps from the known keto acid 4 and followed the course 4-10-11-16- 20-24-25-27-29-+ 36-+ 46-47-48-49-(+)-2; the overall yield was about 1.1%. The first three rings were assembled from keto acid 4 and ketal amine 8, which were coupled to form amide 10. This material was isomerized under acidic conditions to the tricyclic ketal lactam ...