A stereoselective method for the construction of the C8′-O-C6 ether of nigricanoside-A: synthesis of simple models for the C20 lipid chain/galactosyl glycerol segment

TETRAHEDRON LETTERS

卷:54

Article

Kinashi, Naoto¹  Fujiwara, Kenshu¹  Tsunoda, Takayuki¹  Katoono, Ryo¹  Kawai, Hidetoshi¹  Suzuki, Takanori¹ 

[1] Hokkaido Univ, Fac Sci, Dept Chem, Sapporo, Hokkaido 0600810, Japan

关键词: Natural product synthesis;    Monogalactosyl diacyl glycerol;    Ireland-Claisen rearrangement;    Ether lipid;    Stereoselective synthesis;   

DOI  :  10.1016/j.tetlet.2013.06.085

来源: Elsevier

【 摘 要 】

A method for the stereoselective construction of the C8'-O-C6 ether of nigricanoside-A, an antimitotic natural product from the green alga Avrainvillea nigricans, has been developed based on chirality-transferring Ireland-Claisen rearrangement. The method was successfully applied to the synthesis of simple models for the C20 lipid chain/galactosyl glycerol segment of the natural product. (C) 2013 Elsevier Ltd. All rights reserved.

【 授权许可】

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