Enantioselective total synthesis of (-)-denticulatins A and B using a novel group-selective aldolization of a meso dialdehyde as a key step

Jef De Brabander, Wolfgang Oppolzer

Research output: Contribution to journalArticle

23 Scopus citations

Abstract

The diastereoselective synthesis of (-)-denticulatin A (1a) was achieved for the first time in 9 steps (41% yield) based on a novel group-selective aldolization of a meso dialdehyde as a key step. The inherent chirality present in bornanesultam 4 was thus transmitted to the five stereocenters spanning C4-C8 in key intermediate 8. In addition, denticulatin B (1b) was obtained from the common intermediate 8 en route to denticulatin A in 10 steps and 35% overall yield.

Original languageEnglish (US)
Pages (from-to)9169-9202
Number of pages34
JournalTetrahedron
Volume53
Issue number27
DOIs
StatePublished - Jul 7 1997

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Enantioselective total synthesis of (-)-denticulatins A and B using a novel group-selective aldolization of a meso dialdehyde as a key step'. Together they form a unique fingerprint.

  • Cite this