Syntheses of naturally occurring cytotoxic [7.7]paracyclophanes, (-)-cylindrocyclophane A and its enantiomer, and implications for biological activity

Hiroyuki Yamakoshi, Fumiya Ikarashi, Masataka Minami, Masatoshi Shibuya, Tsutomu Sugahara, Naoki Kanoh, Hisatsugu Ohori, Hiroyuki Shibata, Yoshiharu Iwabuchi

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20 Citations (Scopus)

Abstract

The total syntheses of (-)-cylindrocyclophane A (1), a naturally occurring, cytotoxic [7.7]paracyclophane, and its enantiomer have been achieved in an enantiodivergent manner starting from a chiral propargyl alcohol building block using Smith's cross metathesis/ring-closing metathesis protocol as the key step. The biological evaluation of both enantiomers of cylindrocyclophane A (1 and ent-1) and its analogues indicated that the chirality of 1 is irrelevant to its cytotoxicity, which is attributed to the resorcinol motifs embedded in the robust [7.7]paracyclophane framework.

Original languageEnglish
Pages (from-to)3772-3781
Number of pages10
JournalOrganic and Biomolecular Chemistry
Volume7
Issue number18
DOIs
Publication statusPublished - 2009 Sep 7

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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