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

Research output: Contribution to journalArticle

22 Citations (Scopus)

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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Saponification
Oxidation
Acids
naphthosultone

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Enantioselective synthesis of the Prelog-Djerassi lactonic acid via group-selective aldolization/desymmetrization of a meso dialdehyde with a chiral N-propionylsultam. / Oppolzer, Wolfgang; Walther, Eric; Balado, Carlos Pérez; De Brabander, Jef.

In: Tetrahedron Letters, Vol. 38, No. 5, 03.02.1997, p. 809-812.

Research output: Contribution to journalArticle

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