A new construct of the cis-3a-aryloctahydroindole skeleton via the [4+2] cycloaddition of furanyl carbamates

Albert Padwa, Cheryl K. Eidell, Stephen M. Lynch

Research output: Contribution to journalArticle

5 Scopus citations

Abstract

Several 2-methylthio-5-amidofurans containing tethered unsaturation were prepared via the reaction of dimethyl(methylthio)-sulfonium tetrafluoroborate (DMTSF) with β-alkoxy-γ-dithiane amides. Thermolysis of these furans resulted in an intramolecular Diels-Alder reaction (IMDAF). The resulting oxa-bridged cycloadducts underwent a subsequent rearrangement to form bicyclic lactams. Model studies were directed toward mesembrine as well as the core skeleton of the 3,4-benzoerythrinane skeleton. Using this cascade sequence, a formal synthesis of the alkaloid erysotrine was accomplished.

Original languageEnglish (US)
Pages (from-to)227-242
Number of pages16
JournalHeterocycles
Volume58
DOIs
Publication statusPublished - Nov 22 2002
Externally publishedYes

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ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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