Concise stereoselective routes to advanced intermediates related to natural and unnatural pinnaic acid

Matthew W. Carson, Guncheol Kim, Martin F. Hentemann, Dirk Trauner, Samuel J. Danishefsky

Research output: Contribution to journalArticle

Abstract

Important intermediates: In an effort to synthesize and determine the stereo-chemistry of pinnaic acid, C14-epimeric aldehydes 1 and 2 were generated from Meyers' lactam 3. A key step in the parallel syntheses is a highly stereoselective vinylogous Michael cyclization; Boc = tert-butoxy carbonyl, TFA = trifluoro-acetic acid.

Original languageEnglish (US)
Pages (from-to)4450-4452
Number of pages3
JournalAngewandte Chemie - International Edition
Volume40
Issue number23
DOIs
StatePublished - Dec 3 2001

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Trifluoroacetic Acid
Lactams
Stereochemistry
Cyclization
Aldehydes
Acetic acid
Acids
pinnaic acid
tert-butoxy

Keywords

  • Alkaloids
  • Asymmetric synthesis
  • Natural products
  • Total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Concise stereoselective routes to advanced intermediates related to natural and unnatural pinnaic acid. / Carson, Matthew W.; Kim, Guncheol; Hentemann, Martin F.; Trauner, Dirk; Danishefsky, Samuel J.

In: Angewandte Chemie - International Edition, Vol. 40, No. 23, 03.12.2001, p. 4450-4452.

Research output: Contribution to journalArticle

Carson, Matthew W. ; Kim, Guncheol ; Hentemann, Martin F. ; Trauner, Dirk ; Danishefsky, Samuel J. / Concise stereoselective routes to advanced intermediates related to natural and unnatural pinnaic acid. In: Angewandte Chemie - International Edition. 2001 ; Vol. 40, No. 23. pp. 4450-4452.
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