First Total Synthesis of Naturally Occurring (−)??Nitidon and Its Enantiomer

F Bellina, A Carpita, L Mannocci…

Index: Bellina, Fabio; Carpita, Adriano; Mannocci, Luca; Rossi, Renzo European Journal of Organic Chemistry, 2004 , # 12 p. 2610 - 2619

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Citation Number: 24

Abstract

Abstract The first total synthesis of naturally occurring (−)-nitidon and its enantiomer is reported. The best of the routes investigated for preparation of these enantiomerically pure compounds involves a modification of the Cadiot− Chodkiewicz reaction and the Sharpless asymmetric epoxidation of an (E)-2-ene-4, 6-diyn-1-ol as key steps and proceeds in five steps and 18% overall yield. Both enantiomers of nitidon and some related 6-(1, 3-diyn-1- ...