Synthetic studies on duocarmycin. 1. Total synthesis of dl-duocarmycin A and its 2-epimer

Yasumichi Fukuda, Yoshio Itoh, Kazuhiko Nakatani, Terashima Shiro

Research output: Contribution to journalArticle

50 Citations (Scopus)

Abstract

The title synthesis was first achieved by employing novel methoxycarbonylation of the C4-position of the 5-aminoindoline by way of the isatin and subsequent Dieckmann cyclization to the methyl 2-methylindoxyl-2-carboxylate as key steps. In vitro cytotoxicity assay against P388 murine leukemia obviously disclosed that cytotoxicities of the synthesized compounds are comparable and almost half of that of natural (+)-duocarmycin A.

Original languageEnglish
Pages (from-to)2793-2808
Number of pages16
JournalTetrahedron
Volume50
Issue number9
DOIs
Publication statusPublished - Feb 28 1994
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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