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

Organic & Biomolecular Chemistry Pub Date: 2009-07-14 DOI: 10.1039/B909646A

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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