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

49 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

Fingerprint

Isatin
Leukemia P388
Cyclization
Cytotoxicity
Assays
In Vitro Techniques
duocarmycin A

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Synthetic studies on duocarmycin. 1. Total synthesis of dl-duocarmycin A and its 2-epimer. / Fukuda, Yasumichi; Itoh, Yoshio; Nakatani, Kazuhiko; Shiro, Terashima.

In: Tetrahedron, Vol. 50, No. 9, 28.02.1994, p. 2793-2808.

Research output: Contribution to journalArticle

Fukuda, Yasumichi ; Itoh, Yoshio ; Nakatani, Kazuhiko ; Shiro, Terashima. / Synthetic studies on duocarmycin. 1. Total synthesis of dl-duocarmycin A and its 2-epimer. In: Tetrahedron. 1994 ; Vol. 50, No. 9. pp. 2793-2808.
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