A formal synthesis of aplysiatoxin: enantioselective synthesis of kishi's aldehyde

Hiroaki Okamura, Satoru Kuroda, Satoru Ikegami, Kenji Tomita, Yu ichi Sugimoto, Shin ichi Sakaguchi, Yoshio Ito, Tsutomu Katsuki, Masaru Yamaguchi

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26 Citations (Scopus)

Abstract

This paper describes the enantioselective synthesis of key fragments (12, 18, 24, and 35) for the synthesis of aplysiatoxin (1a), a potent cancer promoter, and their convergent assembly to Kishi's aldehyde (2). Since 2 has already been transformed into 1a in a short step, its synthesis constitutes a formal total synthesis of 1a. Synthesis of fragments of aplysiatoxin (1a) and their convergent assembly to the key intermediate, Kishi's aldehyde (2), for the synthesis of 1a are described.

Original languageEnglish
Pages (from-to)10531-10554
Number of pages24
JournalTetrahedron
Volume49
Issue number46
DOIs
Publication statusPublished - 1993

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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    Okamura, H., Kuroda, S., Ikegami, S., Tomita, K., Sugimoto, Y. I., Sakaguchi, S. I., Ito, Y., Katsuki, T., & Yamaguchi, M. (1993). A formal synthesis of aplysiatoxin: enantioselective synthesis of kishi's aldehyde. Tetrahedron, 49(46), 10531-10554. https://doi.org/10.1016/S0040-4020(01)81547-7