A chemo-enzymatic elaboration of a quarternary chiral center: An alternative approach to the side chain of furaquinocin D

Tomohiro Akeboshi, Yoshikazu Ohtsuka, Takeshi Sugai, Hiromichi Ohta

研究成果: Article査読

12 被引用数 (Scopus)

抄録

A new approach to ethyl (2R,3R)-2-t-butyldimethytsilyloxymethyl-3- hydroxy-2-methylbutanoate, a compound which is related to a synthetic intermediate of the side chain of furaquinocin D, is described. The characteristic feature of this compound is a quarternary chiral center and an adjacent secondary alcohol, both of which are in a stereochemically defined state, and the setup of these functionalities was achieved by a combination of stereoselective chemical and enzymatic reactions. The reduction of ethyl 2-hydroxymethyl-2-methyl-3-oxobutanoate with excess NaBH4 afforded (2R*,3R*)-(±)-hydroxy ester with a high diastereomeric excess. After protecting the primary hydroxy group as TBDMS ether, the optical resolution was achieved by lipase-catalyzed hydrolysis of the corresponding chloroacetate in a highly enantioselective manner.

本文言語English
ページ(範囲)7387-7394
ページ数8
ジャーナルTetrahedron
54
26
DOI
出版ステータスPublished - 1998 6月 25

ASJC Scopus subject areas

  • 生化学
  • 創薬
  • 有機化学

フィンガープリント

「A chemo-enzymatic elaboration of a quarternary chiral center: An alternative approach to the side chain of furaquinocin D」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル