Synthetic studies on isoschizogamine: Construction of [3.3.1] bicyclic aminal core by using oxidative skeletal rearrangement This article is dedicated to memory of the late Professor Emeritus Keiichiro Fukumoto

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Abstract

The tetracyclic core structure of isoschizogamine containing aminal functionality was constructed by oxidative skeletal rearrangement of a 1,2-diaminoethene derivative. The 1,2-diaminoethane was prepared by palladium-catalyzed allylation at the 4a position of a 1,2,3,4-tetrahydro- β-carboline derivative and subsequent lactam formation. After the oxidative skeletal rearrangement using dimethyldioxirane, the allyl group was removed by a three-step sequence to provide the tetracyclic core skeleton of isoschizogamine with aminal functionality.

Original languageEnglish
Pages (from-to)7115-7118
Number of pages4
JournalTetrahedron Letters
Volume54
Issue number52
DOIs
Publication statusPublished - 2013 Dec 25

Keywords

  • Alkaloid
  • Allylation
  • Aminal
  • Oxidation
  • Rearrangement

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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