First asymmetric total synthesis of (-)-antofine by using an enantioselective catalytic phase transfer alkylation.
[structure: see text] The first asymmetric total synthesis of a potential antitumor phenanthroindolizidine alkaloid, (-)-antofine, is described. An important feature of this synthesis is the creation of a stereogenic center by using enantioselective catalytic phase transfer alkylation, affording an unnatural alpha-amino acid derivative, together with a ring closing metathesis for pyrrolidine ring construction.
Kim
Sanghee
S
College of Pharmacy, Seoul National University, San 56-1, Shilim, Kwanak, Seoul 151-742, Korea. pennkim@snu.ac.kr
Lee
Jaekwang
J
Lee
Taeho
T
Park
Hyeung-geun
HG
Kim
Deukjoon
D
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000478:Alkylation; D002384:Catalysis; D003500:Cyclization; D007211:Indoles; D010618:Phenanthrolines / Q000138:chemical synthesis* / Q000737:chemistry; D011759:Pyrrolidines / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D007211:Indoles; D010618:Phenanthrolines; D011759:Pyrrolidines; C473343:antofine