Chromium(0)-promoted multicomponent cycloaddition of tethered diynes with cyclic trienes: application to the total synthesis of 9-epi-pentalenic acid.
| Autor: | Rigby JH; Department of Chemistry, Wayne State University, Detroit, Michigan 48202-3489, USA. jhr@chem.wayne.edu, Laxmisha MS, Hudson AR, Heap CH, Heeg MJ |
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| Jazyk: | angličtina |
| Zdroj: | The Journal of organic chemistry [J Org Chem] 2004 Oct 01; Vol. 69 (20), pp. 6751-60. |
| DOI: | 10.1021/jo040204o |
| Abstrakt: | 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. (Copyright 2004 American Chemical Society) |
| Databáze: | MEDLINE |
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