Bocdene and mocdene derivatives of catechols and catecholamines.

Abstract

[reaction in text] 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.