Chromium(0)-promoted multicomponent cycloaddition of tethered diynes with cyclic trienes: application to the total synthesis of 9-epi-pentalenic acid |
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| Authors: | Rigby James H Laxmisha Mundruppady S Hudson Andrew R Heap Charles H Heeg Mary Jane |
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| Affiliation: | Department of Chemistry, Wayne State University, Detroit, Michigan 48202-3489, USA. jhr@chem.wayne.edu |
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| Abstract: | An efficient protecting group controlled regioselective chromium(0)-mediated three-component higher order cycloaddition of tethered diynes with cyclic trienes that generates five rings and six stereogenic centers in one step is described. Following a sequence of reactions featuring a chemoselective Baeyer-Villiger rearrangement and a regioselective cyclopropane hydrogenolysis, the total synthesis of 9-epi-pentalenic acid was achieved. |
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