Total synthesis of (S)-(+)-curcudiol, and (S)-(+)- and (R)-(-)-curcuphenol

被引:29
作者
Ono, M [1 ]
Ogura, Y [1 ]
Hatogai, K [1 ]
Akita, H [1 ]
机构
[1] Toho Univ, Sch Pharmaceut Sci, Funabashi, Chiba 2748510, Japan
关键词
bisabolane sesquiterpene; enantioselective hydrolysis; lipase; total synthesis;
D O I
10.1248/cpb.49.1581
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A highly enantioselective synthesis of the versatile chiral synthons possessing one stereogenic center, (S)-and (R)-4-aryl-5-hydroxy-(2E)-pentenoate (3) was achieved based on the enzymatic reaction of (+/-)-3 with commercially available lipases MY-30 or OF-360 from Candida rugosa. Application of (S)-3 and (R)-3 to the total syntheses of (S)-curcuphenol (1), (S)-curcudiol (2), and (R)-curcuphenol (1), respectively, is described.
引用
收藏
页码:1581 / 1585
页数:5
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