Short synthesis of phenylpropanoid glycosides calceolarioside-B and eutigoside-A

被引：17
作者：
Duc Thinh Khong [1 ]
Judeh, Zaher M. A. [1 ]
机构：
[1] Nanyang Technol Univ, Sch Chem & Biomed Engn, 62 Nanyang Dr,N1-2-B1-14, Singapore 637459, Singapore
来源：
TETRAHEDRON LETTERS | 2017年 / 58卷 / 01期
关键词：
Phenylpropanoid glycosides; Calceolarioside-B; Eutigoside-A; Regioselective acylation; Dimethyltin dichloride; SCANDIUM TRIFLUOROMETHANESULFONATE; SYRINGALIDE-B; ACYLATION; CONSTITUENTS; LEAVES;
D O I：
10.1016/j.tetlet.2016.11.116
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A convenient 4-step synthesis of calceolarioside-B 1 and eutigoside-A 2 in high overall yield is described. The key step involved the regioselective, Me2SnCl2-catalyzed 0-6 acylation of unprotected 2-phenylethyl-beta-D-glucosides 5a-b with cinnamoyl chlorides 6a-b in excellent yields. Acylation at 0-6 is selective with the acid chlorides used. This work serves as a model for the convenient synthesis of phenylpropanoid glycosides acylated at 0-6. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码：109 / 111
页数：3
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