A unified approach to the daucane and sphenolobane bicyclo[5.3.0]decane core: Enantioselective total syntheses of daucene, daucenal, epoxydaucenal B, and 14-para-anisoyloxydauc-4,8-diene
Access to the bicyclo[5.3.0]decane core found in the daucane and sphenolobane terpenoids via a key enone intermediate enables the enantioselective total syntheses of daucene, daucenal, epoxydaucenal B, and 14-para-anisoyloxydauc-4,8-diene. Central aspects include a catalytic asymmetric alkylation followed by a ring contraction and ring-closing metathesis to generate the five- and seven-membered rings, respectively. United front! A route to the bicyclo[5.3.0]decane core of the daucane and sphenolobane terpenoids via a key enone intermediate is described that enables the enantioselective total syntheses of several members of this family of natural products (see scheme). Copyright
Bennett, Nathan B.,Stoltz, Brian M.
supporting information
p. 17745 - 17750
(2014/01/17)
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