Özdemirhan, DevrimSarıçelik, Özlem2021-06-232021-06-2320170957-4166https://doi.org/10.1016/j.tetasy.2016.11.010https://hdl.handle.net/20.500.12491/9312The development of an efficient chemoenzymatic route for the synthesis of optically active dihydroxy cyclopenta[b]naphthalenones; (+)-1,4a-dihydroxy-4a,5,6,7,8,8a,9,9a-octahydro-1H-cyclopenta[b]naphthalen-2(4H)-one (+)-10 and (+)-1,8a-dihydroxy-4a,5,6,7,8,8a,9,9a-octahydro-1H-cydopenta[b]naphthalen-2(4H)-one (+)-11 is described. Different lipases and esterases were tested in the enzymatic hydrolysis of the corresponding acetates (+/-)-4a-hydroxy-2-oxo-2,4,4a,5,6,7,8,8a,9,9a-decahydro-1H-cyclopenta[b]naphthalen-1-yl acetate (+/-)-8, (+/-)-8a-hydroxy-2-oxo-2,4,4a,5,6,7,8,8a,9,9a-decahydro-1H-cyclopenta[b]naphthalen-1-yl acetate (+/-)-9, CRL (Candida Rugosa Lipase) and PLE (Pig Liver Esterase) were found to be the most effectual enzymes; for (-)-8 by 47% ee with the corresponding dihydroxy; (+)-10 by 98% ee in the presence of CRL; whereas, ()-8 was obtained with 40% ee with the corresponding dihydroxy, (+)-10 with 58% ee in the PLE hydrolysis. It was concluded that CRL was the best biocatalyst for the substrate (+/-)-8. Moreover, enzymatic resolution in the presence of CRL yields, (-)-9 with 46% ee with the corresponding dihydroxy derivative; (+)-11 with 98% ee; however, in the presence of PLE, yields (-)-9 with 36% ee as well as the related dihydroxy derivative; (+)-11 with 49% ee respectively. The study concluded that CRL is the best biocatalyst for compounds (+/-)-8 and (+/-)-9. (C) 2016 Elsevier Ltd. All rights reserved.eninfo:eu-repo/semantics/closedAccessActive Dihydroxy Cyclopenta [b]NaphthalenonesChemoenzymatic RouteDecalin-Based Bioactive Natural ProductsArticle10.1016/j.tetasy.2016.11.0102811181242-s2.0-85007039383N/AWOS:000392771200014N/A