Preparative and stereoselective synthesis of the versatile intermediate for carbocyclic nucleosides: effects of the bulky protecting groups to enforce facial selectivity.
The preparative and stereoselective synthesis (45-50% overall yields) of the target compound 17 has been accomplished from D-ribose. The bulky protecting groups such as TBDPS and Trityl enforced the facial selectivity during Grignard reaction to give the tertiary beta-allylic alcohol 16 as the sole product, which was oxidatively rearranged to the key molecule 17 in excellent yield.
Choi
Won Jun
WJ
Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120-750, Korea.
Moon
Hyung Ryong
HR
Kim
Hea Ok
HO
Yoo
Byul Nae
BN
Lee
Jeong A
JA
Shin
Dae Hong
DH
Jeong
Lak Shin
LS
D000241:Adenosine / Q000031:analogs & derivatives / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D015394:Molecular Structure; D009705:Nucleosides / Q000032:analysis / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D012266:Ribose / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D009705:Nucleosides; D012266:Ribose; C031096:neplanocin A; D000241:Adenosine