Enantioselective entry into benzoxabicyclo[2.2.1]heptyl systems via enzymatic desymmetrization

Toward chiral building blocks for lignan synthesis

David B Berkowitz, Jun Ho Maeng

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

The meso diacetate, 9, available in seven steps from piperonal, is efficiently desymmetrized with preferential cleavage of the R-arm-acetate under catalysis by porcine pancreatic lipase in 10% DMSO-phosphate buffer, pH 8. The resulting monoacetate 12, a potentially useful chiral building block for the synthesis of derivatives of the Podophyllum lignans, is obtained in good chemical yield (66-83%) and in high optical yield (95% ee) on a multigram scale.

Original languageEnglish (US)
Pages (from-to)1577-1580
Number of pages4
JournalTetrahedron Asymmetry
Volume7
Issue number6
DOIs
StatePublished - Jan 1 1996

Fingerprint

Podophyllum
Lignans
Lipases
Dimethyl Sulfoxide
Lipase
Catalysis
entry
Buffers
Phosphates
Acetates
Swine
Derivatives
synthesis
catalysis
cleavage
acetates
phosphates
buffers
piperonal

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

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abstract = "The meso diacetate, 9, available in seven steps from piperonal, is efficiently desymmetrized with preferential cleavage of the R-arm-acetate under catalysis by porcine pancreatic lipase in 10{\%} DMSO-phosphate buffer, pH 8. The resulting monoacetate 12, a potentially useful chiral building block for the synthesis of derivatives of the Podophyllum lignans, is obtained in good chemical yield (66-83{\%}) and in high optical yield (95{\%} ee) on a multigram scale.",
author = "Berkowitz, {David B} and Maeng, {Jun Ho}",
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AU - Maeng, Jun Ho

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AB - The meso diacetate, 9, available in seven steps from piperonal, is efficiently desymmetrized with preferential cleavage of the R-arm-acetate under catalysis by porcine pancreatic lipase in 10% DMSO-phosphate buffer, pH 8. The resulting monoacetate 12, a potentially useful chiral building block for the synthesis of derivatives of the Podophyllum lignans, is obtained in good chemical yield (66-83%) and in high optical yield (95% ee) on a multigram scale.

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