The total synthesis of (-)-amathaspiramide F

Chambers C. Hughes, Dirk Trauner

Research output: Contribution to journalArticle

Abstract

Breaking the cis rule: L-Proline and not as expected D-proline led to (-)-amathaspiramide F with the correct configuration in a short sequence of steps (see retrosynthetic scheme). This synthesis features an exception to the principle of self-regeneration of chirality and a strategy for circumventing a problematic Nef reaction in the presence of densely spaced polar functionality.

Original languageEnglish (US)
Pages (from-to)4556-4559
Number of pages4
JournalAngewandte Chemie - International Edition
Volume41
Issue number23
DOIs
StatePublished - Dec 2 2002

Fingerprint

Chirality
Proline
amathaspiramide F

Keywords

  • Alkaloids
  • Amathaspiramides
  • Nef reaction
  • Proline
  • Total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

The total synthesis of (-)-amathaspiramide F. / Hughes, Chambers C.; Trauner, Dirk.

In: Angewandte Chemie - International Edition, Vol. 41, No. 23, 02.12.2002, p. 4556-4559.

Research output: Contribution to journalArticle

Hughes, Chambers C. ; Trauner, Dirk. / The total synthesis of (-)-amathaspiramide F. In: Angewandte Chemie - International Edition. 2002 ; Vol. 41, No. 23. pp. 4556-4559.
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