Synthesis, Absolute Configuration, and Enantioselectivity of Antiretroviral Effect of (R)-(-)-and (S)-(+)-Cytallene. Lipase-Catalyzed Enantioselective Acylations of (.+-.)- …

…, C Simons, S Megati, H Nishimura…

Index: Jones, Bryan C. N. M.; Silverton, James V.; Simons, Claire; Megati, Sreenivasulu; Nishimura, Hisao; et al. Journal of Medicinal Chemistry, 1995 , vol. 38, # 8 p. 1397 - 1405

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Citation Number: 40

Abstract

Enantioselectivity of acylations of (&)-cytallene (lb),(f)-N4-acetylcytallene (lla),(&)-N4- benzoylcytallene (1 lb), and (~)-N4-(9-fluorenylmethoxycarbonyl) cytallene (1 IC) using vinyl butyrate or acetate catalyzed by lipases in organic solvents was investigated. Reactions with lb, lla, and adenallene (la) did not display a high enantioselectivity but all resulted in a predominant acylation of the (-)-enantiomers. Application of the Lowe-Brewster rule led to ...