1192065-27-2Relevant academic research and scientific papers
Syntheses of naturally occurring cytotoxic [7.7]paracyclophanes, (-)-cylindrocyclophane A and its enantiomer, and implications for biological activity
Yamakoshi, Hiroyuki,Ikarashi, Fumiya,Minami, Masataka,Shibuya, Masatoshi,Sugahara, Tsutomu,Kanoh, Naoki,Ohori, Hisatsugu,Shibata, Hiroyuki,Iwabuchi, Yoshiharu
supporting information; experimental part, p. 3772 - 3781 (2009/10/24)
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.
