Total and formal enantioselective synthesis of lyngbic acid and hermitamides A and B
作者:Marie-Alice Virolleaud、Christine Menant、Bernard Fenet、Olivier Piva
DOI:10.1016/j.tetlet.2006.05.078
日期:2006.7
The synthesis of lyngbic acid and both hermitamides A and B, three compounds previously isolated from Lyngbya majuscula has been achieved by a cross-metathesis between 4-methoxyundec-1-ene with pent-4-enoic acid or its amides. The reaction proceeds smoothly to deliver the target molecules in appreciable yields and with a very high E selectivity as determined by NMR experiments. Allyl transfer using
先前从山茱Lyn中分离得到的三种化合物,即lyngbic acid和Hermitamides A和B的合成,是通过4-甲氧基十一碳烯与戊-4-烯酸或其酰胺的交叉复分解实现的。反应顺利进行,以可观的收率递送目标分子,并具有非常高的E选择性(通过NMR实验确定)。使用樟脑衍生的均丙醇进行烯丙基转移,可以合成对映体富集的起始原料。