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

Takeshi Sugai, Hideaki Kakeya, Hiromichi Ohta

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 languageEnglish
Pages (from-to)3463-3468
Number of pages6
JournalTetrahedron
Volume46
Issue number10
DOIs
Publication statusPublished - 1990

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Carbon
Friedel-Crafts reaction
Lipase
Hydrolysis
Esters
mevalonolactone

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

A synthesis of (R)-(-)-mevalonolactone by the combination of enzymatic and chemical methods. / Sugai, Takeshi; Kakeya, Hideaki; Ohta, Hiromichi.

In: Tetrahedron, Vol. 46, No. 10, 1990, p. 3463-3468.

Research output: Contribution to journal › Article

Sugai, T, Kakeya, H & Ohta, H 1990, 'A synthesis of (R)-(-)-mevalonolactone by the combination of enzymatic and chemical methods', Tetrahedron, vol. 46, no. 10, pp. 3463-3468. https://doi.org/10.1016/S0040-4020(01)81516-7
Sugai T, Kakeya H, Ohta H. A synthesis of (R)-(-)-mevalonolactone by the combination of enzymatic and chemical methods. Tetrahedron. 1990;46(10):3463-3468. https://doi.org/10.1016/S0040-4020(01)81516-7
Sugai, Takeshi ; Kakeya, Hideaki ; Ohta, Hiromichi. / A synthesis of (R)-(-)-mevalonolactone by the combination of enzymatic and chemical methods. In: Tetrahedron. 1990 ; Vol. 46, No. 10. pp. 3463-3468.
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