d-生物素的全合成研究

Studies on Total Synthesis of d-Biotin

以L-胱氨酸或L-半胱氨酸的盐酸盐为起始原料,经过10步反应,以超过30%的产率,得到一条新的高效的d-生物素合成路线.从L-胱氨酸开始,通过中间休2的酰胺烷基化得到中间体3,再在过氧酸催化下重排开环生成中间体4,然后经过氧化、还原和缩合等几步建立起生物素的骨架.

A new and highly efficient synthesis of （＋）-biotin which is based on the ready availability of L-cysteine or L-cystine as a chiral starting material has been achieved, which contains 10 steps reactions with over 30% yield. From L-cysteine involving amidoalkylation of hydroxy imidazothiazolone 2 to furnish C-7-substituted imidazo-thiazolones 3, then rearrange and hydrolyze to form 4 by Collins oxidation, reducetion of intermediate 4 and so on, the requisite biotin skeletal structure is established.