Synthesis and lipase-mediated stereoselective deacetylation of (+/-)-3-acetoxymethyl-3-alkyl-7-methoxychroman-4-ones

Authors
Poonam,"Prasad, AK Azim, A Kumar, R Jain, SC Parmar, VS Olsen, CE Errington, W
Citation
Ak. Poonam,"prasad et al., Synthesis and lipase-mediated stereoselective deacetylation of (+/-)-3-acetoxymethyl-3-alkyl-7-methoxychroman-4-ones, TETRAHEDRON, 57(34), 2001, pp. 7395-7402
Citations number
30
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
34
Year of publication
2001
Pages
7395 - 7402
Database
ISI
SICI code
0040-4020(20010820)57:34<7395:SALSDO>2.0.ZU;2-2
Abstract
Six (+/-)-3-acetoxymethyl-3-alkyl-7-methoxychroman-4-ones have been synthes ized in four steps starting with the coupling of resorcinol with correspond ing aliphatic acid leading to the formation of 2,4-dihydroxyphenyl alkyl ke tones, which upon monomethylation and hydroxymethylation, followed by acety lation afforded the racemic acetoxymethylated compounds in 17-30% overall y ields. Candida rugosa lipase-catalyzed deacetylation of (+/-)-3-acetoxymeth ylchromanones in diisopropyl ether exhibited fairly moderate enantioselecti vity. (C) 2001 Elsevier Science Ltd. All rights reserved.