Synthesis of novel spiro[2.3]hexane carbocyclic nucleosides via enzymatic resolution.
[reaction: see text] Novel R- and S-spiro[2.3]hexane nucleosides have been synthesized. The key step involved the Pseudomonas cepacia lipase catalyzed resolution of racemic compound 2, synthesized in seven steps starting from diethoxyketene and diethyl fumarate, to give (+)-acetate 3 and (-)-alcohol 13. (+)-Acetate 3 and (-)-acetate 14 were converted to R- and S-9-(6-hydroxymethylspiro[2.3]hexane)-4-adenine, respectively.
Bondada
Lavanya
L
Department of Pharmaceutical and Biomedical Sciences, College of Pharmacy, The University of Georgia, Athens, Georgia 30602, USA.
Gumina
Giuseppe
G
Nair
Ranjeet
R
Ning
Xing Hai
XH
Schinazi
Raymond F
RF
Chu
Chung K
CK
D000085:Acetates / Q000737:chemistry; D000438:Alcohols / Q000737:chemistry; D016956:Burkholderia cepacia / Q000201:enzymology*; D002384:Catalysis; D005650:Fumarates / Q000737:chemistry; D006586:Hexanes / Q000737:chemistry*; D008049:Lipase / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry*
D000085:Acetates; D000438:Alcohols; D005650:Fumarates; D006586:Hexanes; D009705:Nucleosides; C026385:n-hexane; C035088:diethyl fumarate; D008049:Lipase