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Org. Biomol. Chem., 2009, 7, 3772 - 3781, DOI: 10.1039/b909646a

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 and Yoshiharu Iwabuchi

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.

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