Novel "Reverse Kahne-type glycosylation": Access to O-, N-, and C-linked epipodophyllotoxin conjugates

被引：19

作者：

Berkowitz, DB ^{[1
]}

Choi, SJ ^{[1
]}

Bhuniya, D ^{[1
]}

Shoemaker, RK ^{[1
]}

机构：

[1] Univ Nebraska, Dept Chem, Lincoln, NE 68588 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 08期

关键词：

D O I：

10.1021/ol005732a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Exposure of epipodophyllotoxin C-4-sulfoxides to triflic anhydride, followed by a silyl glycoside, provides a glycoconjugate of the etoposide variety via formal "reverse Kahne glycosylation," To our knowledge, this is the first example of this variant of the Kahne activation method wherein the activating functionality is positioned on the aglycon, rather than on the sugar. Phenols, anilines, or allyl silanes are also efficiently captured at C-4, producing the corresponding O-, N, and C linked lignan conjugates.

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页码：1149 / 1152

页数：4

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