Enantioselective synthesis of the Prelog-Djerassi lactonic acid via group-selective aldolization/desymmetrization of a meso dialdehyde with a chiral N-propionylsultam

Wolfgang Oppolzer, Eric Walther, Carlos Pérez Balado, Jef De Brabander

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Abstract

The group-selective aldolization/desymmetrization of meso dialdehyde 5 with a borylenolate derived from N-propionylbornanesultam ent-2 yields very efficiently lactols 6 with simultaneous generation of four stereogenic centers. Oxidation (6→7) followed by saponification of the sultam moiety (7→4) provided the Prelog-Djerassi lactonic acid 4 in a three step sequence in 61-71% overall yield.

Original languageEnglish (US)
Pages (from-to)809-812
Number of pages4
JournalTetrahedron Letters
Volume38
Issue number5
DOIs
StatePublished - Feb 3 1997

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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