Bifunctional chiral synthons via microbiological methods. 2. optically-active α-hydroxy aldehydes.

✍ Scribed by Yoshihisa Takaishi; Yuh-Lin Yang; Dennis DiTullio; Charles J. Sih

• Publisher: Elsevier Science
• Year: 1982
• Tongue: French
• Weight: 204 KB
• Volume: 23
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)85875-x

✦ Synopsis

A versatile chemical-microbiological approach has been developed for the preparation of chiral a-hydroxy aldehydes via stereoselective reduction of the corresponding a-keto thioacetals or via optical resolution of the racemic a-acetoxy esters. As part of our continued interest in the preparation of intermediates of the arachidonic acid cascade2, we have been concerned with the development of a synthetic procedure to make 5(S)-HPETE3, Lavailable for chemical and enzymatic mechanistic studies. This hydroperoxide, 1, is a key precursor4 in the biosynthesis of the Leukotrienes5 (A, B, C, D, E) from arachidonic acid.

Although small quantities of 1 may be obtained from biochemical incubations3, tedious