The Journal of Organic Chemistry

Synthesis of neolignans via a proposed biosynthetic intermediate. Total synthesis of (.+-.)-futoenone

SR Angle, KD Turnbull

Index: Angle, Steven R.; Turnbull, Kenneth D. Journal of Organic Chemistry, 1993 , vol. 58, # 20 p. 5360 - 5369

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Citation Number: 11

Abstract

The attempted spectroscopic observation of a quinone methide proposed to be an intermediate in the biosynthesis of neolignans is reported. The results afforded substantial indirect evidence for the formation of quinone methide 3. The synthesis of racemic bicyclo [3.2. lloctenedione 22, a natural product, is proposed to occur through a similar quinone methide intermediate. The synthesis of (&)-futoenone via a benzylic cation intermediate ...