Synlett 2005(5): 0869-0871  
DOI: 10.1055/s-2005-863744
LETTER
© Georg Thieme Verlag Stuttgart · New York

First Enantioselective Synthesis of (-)-(2S,6S)-(6-Ethyltetrahydropyran-
2-yl)formic Acid

Leandro S. M. Mirandaa, Bruno A. Meirelesa, Jerônimo S. Costaa, Vera. L. P. Pereiraa, Mário L. A. A. Vasconcellos*b
a Núcleo de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro, Bloco H, CCS, Ilha do Fundão, Rio de Janeiro, RJ, 21941-590, Brasil
b Departamento de Química, Universidade Federal da Paraíba, Campus I, João Pessoa, PB, 58059-900, Brasil
Fax: +55(83)2167413; e-Mail: mlaav@quimica.ufpb.br;
Further Information

Publication History

Received 22 December 2004
Publication Date:
09 March 2005 (online)

Abstract

We describe in this letter the first enantioselective synthesis of (-)-(2S,6S)-(6-ethyltetrahydropyran-2-yl)formic acid (2) in five steps (30% overall yield, 87% ee), from the commercial chiral template (R)-2,3-isopropylideneglyceraldehyde (4). The two stereogenic centers in 2 were controlled by diastereoselective ­Barbier allylation of 4 in aqueous media and an efficient Prins ­cyclization reaction between 5 with propanal.