regioselective protection of the 4-hydroxyl of 3,4-dihydroxy-benzaldehyde的特定选择的保护4-hydroxyl 4-dihydroxy-benzaldehyde.pdfVIP

Molecules 2002, 7, 697-705 molecules ISSN 1420-3049 Regioselective Protection of the 4-Hydroxyl of 3,4-Dihydroxy- benzaldehyde * Guy L. Plourde and Randy R. Spaetzel University of Northern British Columbia, Department of Chemistry, 3333 University Way, Prince George, British Columbia, Canada, V2N 4Z9. Tel: 1-250-960-6694, Fax: 1-250-960-5545. * Author to whom correspondence should be addressed; E-mail: plourde@unbc.ca Received: 30 July 2002; in revised form: 12 September 2002 /Accepted: 14 September 2002 / Published: 30 September 2002 Abstract: The regioselective protection of the 4-hydroxyl group of 3,4-dihydroxy- benzaldehyde was accomplished with seven different protecting groups (benzyl, p- methoxybenzyl, o-nitrobenzyl, 2,6-dichlorobenzyl, 3,4-dichlorobenzyl, vinyl and propargyl) in yields ranging between 67-75%. Keywords: regioselective, protection, catechol, 3,4-dihydroxybenzaldehyde Introduction We recently reported our study of the diastereoselective spiroannulation of simple phenols producing spiroethers 1a-c shown in Figure 1 [1]. In a continuation of this work, we needed to replace the methoxy group with other substituents in order to study the effect these groups would have on the spiroannulation reaction. To accomplish this task, we first needed to selectively protect the 4-hydroxyl group of 3,4-dihydroxybenzaldehyde 2 (Figure 1). Unfortunately, a literature survey showed that little had been done in terms of selective protection of this typ