Stereoselective synthesis of 3-hydroxymethyl-D-cyclopentenone, the versatile intermediate for the synthesis of carbocyclic nucleosides.
The preparative and stereoselective synthesis (45- 50% overall yields, >50 g scale) of the key carbasugars 7a-d was achieved from D-ribose via stereoselective Grignard reaction and oxidative rearrangement as key reactions.
Choi
Won Jun
WJ
WonJun Choi Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120-750, Korea.
Moon
Hyung Ryong
HR
Kim
Hea Ok
HO
Ko
Young Mi
YM
Kim
Hye Jin
HJ
Lee
Jeong A
JA
Lee
Kang Man
KM
Yun
Mi Kyung
MK
Shin
Dae Hong
DH
Chun
Moon Woo
MW
Sheen
Yhun Y
YY
Kim
Kilhyoun
K
Jeong
Lak Shin
LS
D000438:Alcohols / Q000737:chemistry; D002384:Catalysis; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry*; D008956:Models, Chemical; D008967:Molecular Biology / Q000379:methods*; D009705:Nucleosides / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry; D012266:Ribose / Q000737:chemistry; D013237:Stereoisomerism
C506206:3-hydroxymethylcyclopentenone; D000438:Alcohols; D003517:Cyclopentanes; D009705:Nucleosides; D012266:Ribose; C013905:cyclopentenone; D010100:Oxygen