Synlett 2002(12): 2119-2121
DOI: 10.1055/s-2002-35606
LETTER
© Georg Thieme Verlag Stuttgart · New York

Studies Towards Total Synthesis of Antillatoxin: Indium-mediated Allylation Reaction of Carbonyl Compounds with Secondary Allylic Bromide in Aqueous Media

Teck-Peng Loh*, Hong-Yan Song
National University of Singapore, Department of Chemistry, 3 Science Drive 3, Singapore 117543, Singapore
Fax: +6567791691; e-Mail: chmlohtp@nus.edu.sg;
Further Information

Publication History

Received 30 August 2002
Publication Date:
20 November 2002 (online)

Abstract

We have established a new reaction condition for the indium-mediated allylation of an unreactive secondary allylic bromide with aldehydes in aqueous media to afford the corresponding homoallylic alcohols in high yields and syn diastereoselectivity. Furthermore, it has provided an easy entry to the key intermediate for the total synthesis of antillatoxin under mild and environment profitable conditions.