Tetrahedron Asymmetry p. 981 - 996 (1993)
Update date:2022-08-11
Topics:
Tanaka
Yoshioka
Sakai
Rhizopus delemar lipase (RDL)-catalysed hydrolysis of meso-1,3-bis(acetoxymethyl)cyclopentane derivatives (7, 12) and Pseudomonas fluorescens lipase (PFL)-catalysed hydrolysis of 7 afforded the chiral monoacetates (15, 16) of > 99% ee. In explanation of these high enantioselectivities of RDL, the simple box-type active site model of enzyme was tentatively proposed. On the other hand, PFL-catalysed transesterification of meso-bis-(hydroxymethyl)cyclopentane (6) afforded (+)-16 of > 99% ee. The obtained (+) and (-)-16 were converted into the natural carbocyclic nucleoside(-)-aristeromycin (25), respectively.
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