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

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 dia...

Full description

Saved in:
Bibliographic Details
Published inSynlett no. 5; pp. 869 - 871
Main Authors Miranda, LSM, Meireles, BA, Costa, JS, Periera, VLP, Vasconcellos, MLAA
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 21.03.2005
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
enantioselective synthesis
OXIDATION
ALPHA
(R)-2,3-O-isopropylideneglyceraldehyde
ALDEHYDES
PRINS CYCLIZATIONS
STEREOSELECTIVE-SYNTHESIS
Barbier reaction
antinociceptive activity
tetrahydropyran
COPE
Prins cyclization
Online AccessGet more information

Cover

More Information
Summary: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.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2005-863744