Issue 18, 2009
From the journal:

Organic & Biomolecular Chemistry

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

Hiroyuki Yamakoshi,a   Fumiya Ikarashi,a   Masataka Minami,a   Masatoshi Shibuya,a   Tsutomu Sugahara,a   Naoki Kanoh,a   Hisatsugu Ohori,b   Hiroyuki Shibatab  and  Yoshiharu Iwabuchi*a  

* Corresponding authors

a Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aobayama, Sendai, Japan
E-mail: iwabuchi@mail.pharm.tohoku.ac.jp
Fax: +81 22 795 6845

b Department of Clinical Oncology, Institute of Development, Aging and Cancer, Tohoku University, Sendai, Japan

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.

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

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Article information

DOI
https://doi.org/10.1039/B909646A
Article type
Paper
Submitted
15 May 2009
Accepted
16 Jun 2009
First published
14 Jul 2009

Org. Biomol. Chem., 2009,7, 3772-3781

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

H. Yamakoshi, F. Ikarashi, M. Minami, M. Shibuya, T. Sugahara, N. Kanoh, H. Ohori, H. Shibata and Y. Iwabuchi, Org. Biomol. Chem., 2009, 7, 3772 DOI: 10.1039/B909646A

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