Total synthesis of (+)-hygrine via asymmetric phase-transfer catalytic alkylation.
The first enantioselective synthesis of (+)-hygrine (1) is reported. 1 was obtained in 12 steps with 29% overall yield and 97% ee via asymmetric phase-transfer catalytic alkylation and ring-closing metathesis as key steps. The absolute configuration of (+)-hygrine could be directly confirmed as R.
Lee
Jeong-Hee
JH
Research Institute of Pharmaceutical Science and College of Pharmacy, Seoul National University, Seoul 151-742, Korea.
Jeong
Byeong-Seon
BS
Ku
Jin-Mo
JM
Jew
Sang-sup
SS
Park
Hyeung-geun
HG
D000478:Alkylation; D002384:Catalysis; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D011759:Pyrrolidines; C015946:hygrine