A Concise Synthesis of R‐(–)‐Cicutoxin, a Natural 17‐Carbon Polyenyne (Englisch)

in European Journal of Organic Chemistry ; 2009 , 8 ; 1136-1138
European Journal of Organic Chemistry

10.1002/ejoc.200801172.abs

A concise synthesis of the natural polyenyne R‐(–)‐cicutoxin (1) is described. After several trials, the successful synthesis commenced with three key fragments, R‐(–)‐1‐hexyn‐3‐ol (8), 1,4‐diiodo‐1,3‐butadiene (9), and THP‐protected 4,6‐heptadiyn‐1‐ol (6). Sonogashira coupling of compound 9 with acetylenes 6 and 8 gave the 17‐carbon frame, which upon regioselective reduction of a triple bond with Red‐Al and removal of the THP protecting group afforded the natural product in four linear steps. The triply convergent synthesis gave R‐(–)‐cicutoxin in 18 % overall yield. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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