THE ENANTIODIVERGENT TOTAL SYNTHESIS OF NATURAL AND UNNATURAL ENANTIOMERS OF THEOBROXIDE

被引:43
作者
KAMIKUBO, T [1 ]
OGASAWARA, K [1 ]
机构
[1] TOHOKU UNIV,INST PHARMACEUT,SENDAI,MIYAGI 98077,JAPAN
关键词
D O I
10.1016/0040-4039(95)00131-U
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Both enantiomers of theobroxide, a potato micro-tuber inducing substance isolated from Lasiodiplodia theobromae, have been synthesized from a common chiral building block serving as a chiral equivalent of 1,4-dihydroxy-2,5-cyclohexadiene. The synthesis has verified the proposed structure and the absolute configuration.
引用
收藏
页码:1685 / 1688
页数:4
相关论文
共 19 条
[1]  
Nakamori, Matsuura, Yoshihara, Ichihara, Koda, Phytochemistry, 35, (1994)
[2]  
Ogasawara, Pure & Appl. Chem., 66, (1994)
[3]  
Takano, Moriya, Ogasawara, Concise enantiodivergent synthesis of eutypoxide B, Journal of the Chemical Society, Chemical Communications, (1993)
[4]  
Takano, Higashi, Kamikubo, Moriya, Ogasawara, Enantiocontrolled synthesis of optically pure 5-trimethylsilyl- and 5-tributylstannyl-cyclohex-2-enones, Journal of the Chemical Society, Chemical Communications, (1993)
[5]  
Takano, Moriya, Kamikubo, Hiroya, Ogasawara, Tetrahedron Lett., 34, (1993)
[6]  
Takano, Kamikubo, Moriya, Ogasawara, Synthesis, (1994)
[7]  
Kamikubo, Ogasawara, Chem. Lett., (1995)
[8]  
Takano, Higashi, Kamikubo, Moriya, Ogasawara, Synthesis, (1993)
[9]  
Takano, Moriya, Higashi, Ogasawara, Enantiodivergent route to conduritol C via lipase-mediated asymmetrization, Journal of the Chemical Society, Chemical Communications, (1993)
[10]  
Cf. Grieco, Nishizawa, Oguri, Burke, Marinovic, Sesquiterpene lactones: total synthesis of (.+-.)-vernolepin and (.+-.)-vernomenin, Journal of the American Chemical Society, 99, (1977)