Bocdene and mocdene derivatives of catechols and catecholamines

被引：16

作者：

Ariza, X

Pineda, O

Vilarrasa, J

Shipps, GW

Ma, Y

Dai, XD

机构：

[1] Univ Barcelona, Fac Quim, Dept Quim Organ, E-08028 Barcelona, Catalonia, Spain

[2] NeoGenesis Drug Discovery, Cambridge, MA 02139 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 09期

关键词：

D O I：

10.1021/ol015754c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Catechols react chemoselectively, in the presence of either alcohols, 1,2-diols, or simple phenols, with tert-butyl propynoate and with methyl propynoate to give 2-Boc-ethylidene (Bocdene) and 2-Moc-ethylidene (Mocdene) acetals, respectively, in 96-100% yields within 30 min at room temperature, provided that 150 mol % of DMAP is added. Cleavage of these acetals with pyrrolidine readily takes place (at room temperature!) in 95-100% yields, By taking advantage of the features of Bocdene acetals, novel catecholamine-related phosphate mimetics have been prepared.

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页码：1399 / 1401

页数：3

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