Enzyme-catalysed kinetic resolution of 4-endo-hydroxy-2-oxabicyclo[3.3.0]oct-7-en-3-one and employment of the pure enantiomers for the synthesis of anti-viral and hypocholestemic agents

✍ Scribed by Rosemary A. MacKeith; Ray McCague; Horacio F. Olivo; Stanley M. Roberts; Stephen J.C. Taylor; Hui Xiong

• Publisher: Elsevier Science
• Year: 1994
• Tongue: English
• Weight: 968 KB
• Volume: 2
• Category: Article
• ISSN: 0968-0896
• DOI: 10.1016/0968-0896(94)80005-7

✦ Synopsis

endo-hydroxylactone

(k)-(l) was resolved by enantioselective acetylation using CundicIQ cylindracea lipase or preferentially Pseudomonus jkwvscens lipase (pfl). Alternatively the corresponding butyrate (f)-( 3) was hydrolysed with pfl to give the ester (+)-(lS,4R,SS)-( 3) and the alcohol (-)-(lR,4S,5R)-( 1). The latter compound was converted into carbovir (-)-(lR,4S)-( 12) while the ester (+)-( 3) was transformed into the Nactone (+)-(3R,5S)-( 18). The exe-hydroxylactone (k)-( 2) was resolved less efficiently by a trans-esterification process employing pfl and vinyl acetate.