Synthetic studies toward isoschizogamine: Construction of pentacyclic core structure

Kenji Sugimoto, Hiroaki Fujiwara, Akihiro Takada, Dong Gil Kim, Hirofumi Ueda, Hidetoshi Tokuyama

Research output: Contribution to journalArticlepeer-review

Abstract

Development of a concise construction of the pentacyclic core skeleton of isoschizogamine was described. Tetracyclic A,B,D,F-rings structure was assembled by intramolecular aza-Diels–Alder reaction via an ortho-iminoquinone methide intermediate. The C-ring was formed by oxidation of the benzylic position with a combination of Cr(CO)6 and t-BuOOH, followed by the introduction of an aminoethyl side chain, C–H oxidation of the lactam ring with CrO3 and n-Bu4NI, and final cyclization to construct the cyclic aminal moiety.

Original languageEnglish
Pages (from-to)1028-1049
Number of pages22
JournalHeterocycles
Volume97
Issue number2
DOIs
Publication statusPublished - 2018

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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