A concise entry to the skeleton of the tremulane sesquiterpenes is described that culminated in the first enantioselective syntheses of tremulenediol A and tremulenolide A. The approach features a series of efficient transition metal-catalyzed reactions commencing with an enantioselective rhodium(II)-catalyzed intramolecular cyclopropanation followed by a regioselective allylic alkylation and a diastereoseleclive rhodium(l)-catalyzed [5+2] cycloaddition. (c) 2006 Elsevier Ltd. All rights reserved.
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Univ Cardenal Herrera CEU, Dept Farm, C Ramon y Cajal S-N, Valencia 46115, SpainUniv Cardenal Herrera CEU, Dept Farm, C Ramon y Cajal S-N, Valencia 46115, Spain
Vidal-Albalat, Andreu
Matos Paz, Bruno
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Univ Sao Paulo, Inst Chem, Dept Fundamental Chem, Ave Prof Lineu Prestes 748, BR-05508000 Sao Paulo, BrazilUniv Cardenal Herrera CEU, Dept Farm, C Ramon y Cajal S-N, Valencia 46115, Spain