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

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)7387-7394
Number of pages8
JournalTetrahedron
Volume54
Issue number26
DOIs
Publication statusPublished - 1998 Jun 25

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Lipase
Ether
Hydrolysis
Esters
Alcohols
alpha-ketoisovalerate
furaquinocin D
chloroacetic acid

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

A chemo-enzymatic elaboration of a quarternary chiral center : An alternative approach to the side chain of furaquinocin D. / Akeboshi, Tomohiro; Ohtsuka, Yoshikazu; Sugai, Takeshi; Ohta, Hiromichi.

In: Tetrahedron, Vol. 54, No. 26, 25.06.1998, p. 7387-7394.

Research output: Contribution to journalArticle

Akeboshi, Tomohiro ; Ohtsuka, Yoshikazu ; Sugai, Takeshi ; Ohta, Hiromichi. / A chemo-enzymatic elaboration of a quarternary chiral center : An alternative approach to the side chain of furaquinocin D. In: Tetrahedron. 1998 ; Vol. 54, No. 26. pp. 7387-7394.
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