Acyclic diastereoselection as a synthetic route to quassinoids: A Claisen rearrangement based strategy for bruceantin

FE Ziegler, SI Klein, UK Pati…

Index: Ziegler; Klein; Pati; Wang Journal of the American Chemical Society, 1985 , vol. 107, # 9 p. 2730 - 2737

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Citation Number: 48

Abstract

Abstract: A highly stereoselective Claisen rearrangement of allyl vinyl ether 17 gives rise to@-keto ester 18 having the correct relative stereochemistry at Cg, Cp, and C14 of the quassinoids. Efficient, rapid assembly of rings C, D, and E is achieved. The model sets the stage for an eventual synthesis of (-)-bruceantin from keto acid 9b.