(R)-(-)-and (S)-(+)-Adenallene: synthesis, absolute configuration, enantioselectivity of antiretroviral effect, and enzymic deamination.

S Megati, Z Goren, JV Silverton, J Orlina…

Index: Megati, Sreenivasulu; Goren, Zafrir; Silverton, James V.; Orlina, Joel; Nishimura, Hisao; et al. Journal of Medicinal Chemistry, 1992 , vol. 35, # 22 p. 4098 - 4104

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Citation Number: 35

Abstract

Synthesis of optically pure (-1-and (+)-adenallene 2 and 3 is described. Racemic adenallene (la) was subjected to deamination with adenosine deaminase monitored by HPLC using a Chiralcel CA-1 column to give (-)-ademIlene (2) and (+)-hypoxallene (4). The latter compound was converted to acetate 5. The reaction of 5 with trifluoromethanesulfonic anhydride and pyridine followed by ammonolysis furnished acetate 6 or (+)-adenallene (3 ...