Enantioselective Total Synthesis of a Natural Norsesquiterpene of the Calamenene Group by a Silane-Terminated Intramolecular Heck Reaction
- 1 June 1995
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1995 (06) , 597-598
- https://doi.org/10.1055/s-1995-5016
Abstract
The total synthesis of the natural norsesquiterpene 7-desmethyl-2-methoxycalamenene 1 by an enantioselective silane-terminated Heck reaction is described. The substrate 2 used for the Heck reaction was synthesized in 7 steps from 3-(3-methoxyphenyl)propanol in 41 % yield. Heck reaction of 2 with Pd2(dba)3⋅CHCl3, (R)-BINAP and Ag3PO4 gives 8 in 91 % yield with 92 % ee, which after hydroxylation, transformation in the p-toluenesulfonate and methylation with Me2CuLi gave 1 in 36 % yield.Keywords
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