Asymmetric synthesis of (-)-denticulatins A and B via group-selective aldolization of a meso dialdehyde with a chiral N-propionylsultam

Wolfgang Oppolzer, Jef De Brabander, Eric Walther, Gérald Bernardinelli

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Abstract

Aldolization of meso dialdehyde 3 with a borylenolate obtained from chiral N-propionylsultam 4 yields efficiently lactols 5 with simultaneous generation of five stereogenic centers.Dithioketalization/O-desilylation of 5 affords acyclic diol 9 which is converted into the marine polypropionates 1a and 1b via the asymmetric alkylation of N-propionyltoluenesultam 11 and the aldol coupling 10 + 15 → 16.

Original languageEnglish (US)
Pages (from-to)4413-4416
Number of pages4
JournalTetrahedron Letters
Volume36
Issue number25
DOIs
Publication statusPublished - Jun 19 1995

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ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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