A synthesis of (R)-(-)-mevalonolactone by the combination of enzymatic and chemical methods

Takeshi Sugai; Hideaki Kakeya; Hiromichi Ohta

doi:10.1016/S0040-4020(01)81516-7

A synthesis of (R)-(-)-mevalonolactone by the combination of enzymatic and chemical methods

Takeshi Sugai, Hideaki Kakeya, Hiromichi Ohta

School of Pharmaceutical Sciences

Research output: Contribution to journal › Article

34 Citations (Scopus)

Abstract

(R)-(-)-Mevalonolactone was synthesized starting from a chiral tertiary α-benzyloxy ester, obtained by the lipase-catalyzed enantioselective hydrolysis of the corresponding racemate, in 7 steps and 21.5% overall yield. Intramolecular Friedel-Crafts reaction of an intermediate worked well as the key-step for the new carbon-carbon bond formation.

Original language	English
Pages (from-to)	3463-3468
Number of pages	6
Journal	Tetrahedron
Volume	46
Issue number	10
DOIs	https://doi.org/10.1016/S0040-4020(01)81516-7
Publication status	Published - 1990

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ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Cite this

Sugai, T., Kakeya, H., & Ohta, H. (1990). A synthesis of (R)-(-)-mevalonolactone by the combination of enzymatic and chemical methods. Tetrahedron, 46(10), 3463-3468. https://doi.org/10.1016/S0040-4020(01)81516-7

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N2 - (R)-(-)-Mevalonolactone was synthesized starting from a chiral tertiary α-benzyloxy ester, obtained by the lipase-catalyzed enantioselective hydrolysis of the corresponding racemate, in 7 steps and 21.5% overall yield. Intramolecular Friedel-Crafts reaction of an intermediate worked well as the key-step for the new carbon-carbon bond formation.

AB - (R)-(-)-Mevalonolactone was synthesized starting from a chiral tertiary α-benzyloxy ester, obtained by the lipase-catalyzed enantioselective hydrolysis of the corresponding racemate, in 7 steps and 21.5% overall yield. Intramolecular Friedel-Crafts reaction of an intermediate worked well as the key-step for the new carbon-carbon bond formation.

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10.1016/S0040-4020(01)81516-7