Gamma-lactam synthesis via C-H insertion: elaboration of N-benzyl protecting groups for high regioselectivity toward the total synthesis of rolipram.
By intramolecular C-H insertion of alpha-diazo-alpha-(phenylsulfonyl)acetamides, gamma-lactams such as the antidepressant agent rolipram were efficiently synthesized in a highly regioselective manner. N-Benzyl moieties were elaborated as amide protecting groups to enhance regioselectivity in C-H activation as well as chemoselectivity over addition reactions. [reaction: see text]
Yoon
Cheol Hwan
CH
Department of Chemistry (SCA 400), University of South Florida, 4202 E. Fowler Avenue, Tampa, FL 33620-5250, USA.
Nagle
Advait
A
Chen
Chiliu
C
Gandhi
Drashti
D
Jung
Kyung Woon
KW
D000081:Acetamides / Q000737:chemistry; D000928:Antidepressive Agents / Q000138:chemical synthesis; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D020889:Rolipram / Q000138:chemical synthesis*; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism; D014050:Toluene / Q000031:analogs & derivatives
D000081:Acetamides; D000928:Antidepressive Agents; D007769:Lactams; D012997:Solvents; D014050:Toluene; D020889:Rolipram