高等学校化学学报

高等学校化学学报 ›› 2000, Vol. 21 ›› Issue (S1): 510.

• Synthetic Sciences • 上一篇    下一篇

Synthesis the Analog of Strictosidine and Vincoside from Geniposide

LIU Jian-Li, XU Shou-Ning, CHEN Hui, YANG Wen-Zhen   

  1. Department of Chemistry, Xiamen University, Xiamen 361005
  • 出版日期:2000-12-31 发布日期:2000-12-31

Synthesis the Analog of Strictosidine and Vincoside from Geniposide

LIU Jian-Li, XU Shou-Ning, CHEN Hui, YANG Wen-Zhen   

  1. Department of Chemistry, Xiamen University, Xiamen 361005
  • Online:2000-12-31 Published:2000-12-31

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摘要：

Strictosidine (1), a well-known monoterpene indole alkaloid glycoside[1,2], is the precursor and building stone of nearly 2200 indole and related alkaloids and was first isolated by G. N. Smith from Rhazya[3]. It is constructed in vivo from secologanin (2) and tryptamine (3) by plant species[1], as well as in vitro in the presence of the enzyme strictosidine synthase, or under biomimetic conditions in aqueous solution at pH 4.5 (Scheme 1). In the coupling reaction, a new chiral center is formed with complete stereoselectivity in the presence of the enzyme, or together with vincoside (4) in a 1:1 ratio in the absence of the enzyme. Here we describe the preparation of the analog of strictosidine and vincoside from geniposide via the biomimetic conditions. 7 and 8 can be used as the starting material to synthesize other analogs of indole and related alkaloids.

Abstract:

Strictosidine (1), a well-known monoterpene indole alkaloid glycoside[1,2], is the precursor and building stone of nearly 2200 indole and related alkaloids and was first isolated by G. N. Smith from Rhazya[3]. It is constructed in vivo from secologanin (2) and tryptamine (3) by plant species[1], as well as in vitro in the presence of the enzyme strictosidine synthase, or under biomimetic conditions in aqueous solution at pH 4.5 (Scheme 1). In the coupling reaction, a new chiral center is formed with complete stereoselectivity in the presence of the enzyme, or together with vincoside (4) in a 1:1 ratio in the absence of the enzyme. Here we describe the preparation of the analog of strictosidine and vincoside from geniposide via the biomimetic conditions. 7 and 8 can be used as the starting material to synthesize other analogs of indole and related alkaloids.

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