A formal total synthesis of (+/-)-neplanocin A.
Stereoselective formal synthesis of (+/-)-neplanocin A from a cyclopentane derivative employing an elegant strategy involving reiterative usage of an already existing acetonide protecting group is reported. The acetonide protecting group that is carried forward intact right from the starting adduct to an advanced intermediate is shuffled around twice as in a "relay race" through the synthetic sequence, thus avoiding unnecessary employment of additional protecting groups.
Department of Chemistry, Indian Institute of Technology, Kanpur-208 016, India. faiz@iitk.ac.in
Faiz Ahmed
FA
Khan
Bhimsen
B
Rout
D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure
D000970:Antineoplastic Agents; D000998:Antiviral Agents; C031096:neplanocin A; D000241:Adenosine