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

16 Scopus citations

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 - Jun 1996

ASJC Scopus subject areas

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

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