Daphniphyllum alkaloids. 11. Biomimetic total synthesis of methyl homosecodaphniphyllate. Development of the tetracyclization reaction

CH Heathcock, MM Hansen, RB Ruggeri…

Index: Heathcock, Clayton H.; Hansen, Marvin M.; Ruggeri, Roger B.; Kath, John C. Journal of Organic Chemistry, 1992 , vol. 57, # 9 p. 2544 - 2553

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Citation Number: 66

Abstract

A biomimetic total synthesis of (*)-methyl homosecodaphniphyllate has been developed. The synthesis starts with a triply convergent, tandem Michael addition-nolate alkylation, wherein amide 9, enoate 7, and alkyl iodide 5 are assembled in essentially quantitative yield to obtain compounds 13, 14, and 15. The major isomer 13 is converted in three steps into a 1: l mixture of diols 18a and 18b. These diols are subjected to a two-step process ...