Facile synthesis of 9-[(1 ' R,2 ' S)-2 '-hydroxy-3 '-oxocyclopentan-1 '-yl]-9-H-adenine possessing inhibitory activity against human recombinant S-adenosyl-L-homocysteine hydrolase

Treatment of 4'-O-methanesulfonyl-2',3'-O-isopropylideneoraisteromycin with KOBut gave the corresponding 3',4'-dehydro derivative, and subsequent depr otection resulted in the formation of 9-[(1'R,2'S)-2'-hydroxy-3'-oxocyclope ntan-1'-yl]-9-H-adenine possessing inhibitory activity against human recomb inant S-adenosyl-L homocysteine hydrolase (EC 3.3.1.1). In sharp contrast t o KOBut, when lithium azide was adopted as a base, 9-[(1'R,2'S,3'R)-2',3'-O -isopropylidened ioxy-4'-cyclopenten-1'-yl]-H-adenine was selectively obtai ned, and subsequent deprotection afforded DHCeA, which is a well-known pote ntial antiviral agent. (C) 2001 Elsevier Science Ltd. All rights reserved.