Novel sequential sigmatropic rearrangements of allylic diols: application to the total synthesis of (-)-kainic acid

Katsunori Kitamoto; Mana Sampei; Yasuaki Nakayama; Takaaki Sato; Noritaka Chida

doi:10.1021/ol1026602

Novel sequential sigmatropic rearrangements of allylic diols: application to the total synthesis of (-)-kainic acid

Org Lett. 2010 Dec 17;12(24):5756-9. doi: 10.1021/ol1026602. Epub 2010 Nov 24.

Authors

Katsunori Kitamoto¹, Mana Sampei, Yasuaki Nakayama, Takaaki Sato, Noritaka Chida

Affiliation

¹ Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.

PMID: 21105709
DOI: 10.1021/ol1026602

Abstract

Sequential sigmatropic rearrangements (Claisen/Claisen and Claisen/Overman) of enantiopure allylic diols are described. The reactions proceeded in complete diastereoselectivity without protecting group manipulations. The sequential Claisen/Overman rearrangement was successfully applied to the total synthesis of (-)-kainic acid.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Allyl Compounds / chemistry*
Kainic Acid / chemical synthesis*
Molecular Structure
Stereoisomerism

Substances

Allyl Compounds
Kainic Acid