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 Citations (Scopus)

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
StatePublished - Nov 22 2002
Externally publishedYes

Fingerprint

Furans
Lactams
Thermolysis
Carbamates
Cycloaddition
Cycloaddition Reaction
Alkaloids
Skeleton
Amides
mesembrine
dimethyl(methylthio)sulfonium
alkoxyl radical
dithiane
1,2-dimethyltetraselenafulvalene

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

Cite this

A new construct of the cis-3a-aryloctahydroindole skeleton via the [4+2] cycloaddition of furanyl carbamates. / Padwa, Albert; Eidell, Cheryl K; Lynch, Stephen M.

In: Heterocycles, Vol. 58, 22.11.2002, p. 227-242.

Research output: Contribution to journalArticle

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