Sterically biased 3,3-sigmatropic rearrangement of chiral allylic azides: application to the total syntheses of alkaloids |
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Authors: | Lauzon Sophie Tremblay François Gagnon David Godbout Cédrickx Chabot Christine Mercier-Shanks Catherine Perreault Stéphane DeSève Hélène Spino Claude |
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Institution: | Université de Sherbrooke, Département de Chimie, 2500 Boulevard Université, Sherbrooke, Quebec, Canada, J1K 2R1. |
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Abstract: | We describe a tandem Mitsunobu/3,3-sigmatropic rearrangement of allylic azides on a chiral auxiliary system that favors one regioisomer thanks to its exceptional steric bias. The sequence may be completed by the oxidative cleavage of the auxiliary or by a ring-closing metathesis reaction that produces a carbo- or heterocycle directly and a recyclable form of the chiral auxiliary. Applications of the methodology to the total synthesis of (+)-coniine, (+)-lentiginosin, and (+)-pumiliotoxin C are reported. |
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