(-)-Blastmycinolactol (1b) has been prepared in an enantioselective fashion from acetylenic acid 5 by a three step sequence involving debenzylation-lactonization, hydration with concurrent C-3-epimerization, and Baeyer-Villiger oxidation accompanied by ester cleavage. Acylation of 1b with isovaleryl chloride then afforded (+)-blastmycinone (1a) in excellent overall yield. (C) 1997 Elsevier Science Ltd.
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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