951161-65-2Relevant academic research and scientific papers
Enantioselective synthesis of a trans-7,8-dimethoxycalamenene
Werle, Susen,Fey, Thorsten,Neudoerfl, Joerg M.,Schmalz, Hans-Guenther
, p. 3555 - 3558 (2008/02/12)
trans-7,8-Dimethoxy-11,12-dehydrocalamenene, a projected intermediate for the total synthesis of marine serrulatane and amphilectane diterpenes, was efficiently synthesized. Starting from a styrene, asymmetric Rh-catalyzed hydroboration using a novel chiral P.P-bidentate ligand afforded an organoboron intermediate (93% ee) which was directly used for C-C bond formation (double homologation, Suzuki coupling). The 1,4-trans-disubstituted tetralin skeleton was selectively formed by a Friedel-Crafts-type catlonic cyclization under strictly aprotic conditions (Me2AlCl) to suppress a remarkable proton-catalyzed disproportionation via diastereoselective hydride transfer.
