First enantioselective synthesis of (-)-(2S,6S)-(6-ethyltetrahydropyran-2-yl)formic acid

被引：27

作者：

Miranda, LSM

Meireles, BA

Costa, JS

Periera, VLP

Vasconcellos, MLAA

机构：

[1] Univ Fed Paraiba, Dept Quim, BR-58059900 Joao Pessoa, Paraiba, Brazil

[2] Univ Fed Rio de Janeiro, Nucleo Pesquisas Prod Nat, BR-21941590 Rio De Janeiro, Brazil

来源：

SYNLETT | 2005年 / 05期

关键词：

enantioselective synthesis; antinociceptive activity; tetrahydropyran; Prins cyclization; Barbier reaction; (R)-2,3-O-isopropylideneglyceraldehyde;

D O I：

10.1055/s-2005-863744

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：869 / 871

页数：3

共 31 条

[1]

ADAMS DR, 1977, SYNTHESIS-STUTTGART, P661

[2] Aromatic 4-tetrahydropyranyl and 4-quinuclidinyl cations. Linking prins with Cope and Grob [J].