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有机化学
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有机化学 ›› 2006, Vol. 26 ›› Issue (9): 1309-1312. 上一篇    下一篇

研究简报

d-生物素的全合成研究

陈克喜*,a，程向炜b，金佳敏a，盛柳青c   

  1. (a浙江工业大学药学院 杭州 310014)
    (b浙江公安高等专科学校 杭州 310053)
    (c金华职业技术学院药学系 金华 321007)
  • 收稿日期:2005-12-15 修回日期:2006-02-08 发布日期:2006-09-11
  • 通讯作者: 陈克喜

Studies on Total Synthesis of d-Biotin

CHEN Ke-Xi*,a,CHENG Xiang-Weib,JING Jia-Mina,SHENG Liu-Qingc   

  1. (a College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014)
    (b Zhejiang Public Security College, Hangzhou 310053)
    (c Department of Pharmaceutical Science, Jinhua College Profession and Technology, Jinhua 321007)
  • Received:2005-12-15 Revised:2006-02-08 Published:2006-09-11
  • Contact: CHEN Ke-Xi

PDF

1739

被引次数

13

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.

关键词: L-半胱氨酸, d-生物素, 酰胺烷基化

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.

Key words: amidoalkylation, L-cysteine, d-biotin