An Asymmetric Total Synthesis of Picrotoxinin through a Mizoroki–Heck Reaction

Abstract

An asymmetric total synthesis of picrotoxinin was achieved, with a Mizoroki-Heck reaction of an enantioenriched tricyclic lactone with isopropenyl bromide as the key transformation, enabling the highly diastereoselective introduction of the requisite C4-isopropenyl group. After functional group manipulations including carbonylation, bromoetherification, epoxidation and dihydroxylation, picrotoxinin was obtained in moderate to good yield.

Total Synthesis of (+)-Coriamyrtin via a Desymmetrizing Strategy Involving a 1,3-Cyclopentanedione Moiety

“…Picrotoxane-type sesquiterpenes bear a cis -hydrindane skeleton as a common structure, and its bicyclic core is highly oxy-functionalized with hydroxy groups, lactones, and epoxides. Owing to the intriguing biological and structural features of 1 , the Corey, Yamada, Yoshikoshi, Trost, Shenvi, and Nakazaki groups have reported the total synthesis of 1 .…”

Total Synthesis of (+)-Coriamyrtin via a Desymmetric Strategy of a 1,3-Cyclopentanedione Moiety

“…[4] Picrotoxanetype sesquiterpenes bear a cis-hydrindane skeleton as a common structure, and its bicyclic core is highly oxy-functionalized by hydroxy groups, lactones, and epoxides. Owing to the intriguing biological and structural features of 1, Corey et al, [5] Yamada et al, [6] Yoshikoshi et al, [7] Trost et al, [8] Shenvi et al, [9] and Nakazaki et al [10] reported the total synthesis of 1.…”