A pericyclic cascade to the stereocontrolled synthesis of 9-cis-retinoids

B Iglesias, A Torrado, AR de Lera…

Index: Iglesias, Beatriz; Torrado, Alicia; De Lera, Angel R.; Lopez, Susana Journal of Organic Chemistry, 2000 , vol. 65, # 9 p. 2696 - 2705

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Citation Number: 19

Abstract

A domino reaction that is pericyclic in nature is thought to be triggered upon treatment of alkenynol 10 with arylsulfenyl chlorides. The process comprises an ordered sequence of sigmatropic rearrangements: a reversible [2, 3]-allyl sulfenate to allyl sulfoxide shift, followed by a [2, 3]-propargyl sulfenate to allenyl sulfoxide rearrangement, and last a stereodifferentiating [1, 5]-sigmatropic hydrogen migration leading to polyene 13. The ...