Meroquinene (+)-1 was prepared in an efficient and stereocontrolled fashion from (1R-2S)-4-cyclohexene dimethanol monoacetate (-)-8. Key steps are the enzyme-catalyzed hydrolysis of the available diacetate 5 to (-)-8 and of the intermediate diester 17 to hemiester 18, which allow the stereo- and regiocontrolled elaboration of the vicinal vinyl and carboxymethyl groups.
AN EFFICIENT CHEMOENZYMATIC APPROACH TO (+)-MEROQUINENE / B. DANIELI, G. LESMA, M. MAURO, G. PALMISANO, D. PASSARELLA. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 1:11(1990), pp. 793-800. [10.1016/S0957-4166(00)80445-0]
AN EFFICIENT CHEMOENZYMATIC APPROACH TO (+)-MEROQUINENE
B. DANIELIPrimo
;G. LESMASecondo
;D. PASSARELLAUltimo
1990
Abstract
Meroquinene (+)-1 was prepared in an efficient and stereocontrolled fashion from (1R-2S)-4-cyclohexene dimethanol monoacetate (-)-8. Key steps are the enzyme-catalyzed hydrolysis of the available diacetate 5 to (-)-8 and of the intermediate diester 17 to hemiester 18, which allow the stereo- and regiocontrolled elaboration of the vicinal vinyl and carboxymethyl groups.
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