Chonticha MasusaiDarunee SoorukramChutima KuhakarnPatoomratana TuchindaChaveng PakawatchaiVichai ReutrakulManat PohmakotrMahidol UniversityPrince of Songkla University2018-06-112018-06-112012-10-01Helvetica Chimica Acta. Vol.95, No.10 (2012), 1912-1927152226750018019X2-s2.0-84867706563https://repository.li.mahidol.ac.th/handle/20.500.14594/13601The Morita-Baylis-Hillman (MBH) reactions of (4S,5R,7R,8R)- and (4R,5R,7R,8R)-4-hydroxy-7,8-dimethoxy-7,8-dimethyl-6,9-dioxaspiro[4.5] dec-2-en-1-ones (2 and 3, resp.) with aldehydes using various catalysts were studied. A combination of Bu 3 P/phenol in THF was found being optimum conditions giving the corresponding MBH adducts with high diastereoisomeric ratios. After separation, each stereomerically pure isomer of the MBH adducts was subjected to hydrolysis employing 1% aq. CF 3 COOH (TFA) in a water bath of an ultrasonic cleaner to afford the corresponding polyhydroxylated cyclopentenones in good yields. Copyright © 2012 Verlag Helvetica Chimica Acta AG, Zürich, Switzerland.Mahidol UniversityBiochemistry, Genetics and Molecular BiologyChemical EngineeringChemistryPharmacology, Toxicology and PharmaceuticsArticleSCOPUS10.1002/hlca.201200421