Asymmetric total syntheses of (-)-antofine and (-)-cryptopleurine using (R)-(E)-4-(tributylstannyl)but-3-en-2-ol.
The asymmetric total syntheses of the representative phenanthroindolizidine and phenanthroquinolizidine alkaloids, (-)-antofine and (-)-cryptopleurine, are described. An efficient synthetic pathway to the key intermediate 12, in enantiomerically pure form, was achieved by using a chiral building block (R)-9 and the Overman rearrangement with a total transfer of chirality. The problem of constructing the pyrrolidine and piperidine rings was successfully addressed, primarily by using a ring-closing metathesis reaction and a cross-metathesis reaction, respectively.
Kim
Sanghee
S
College of Pharmacy, Seoul National University, San 56-1, Shilim, Kwanak, Seoul 151-742, Korea.
Lee
Taeho
T
Lee
Eunjung
E
Lee
Jaekwang
J
Fan
Gao-jun
GJ
Lee
Sang Kook
SK
Kim
Deukjoon
D
D000470:Alkaloids / Q000138:chemical synthesis*; D000478:Alkylation; D000818:Animals; D000440:Butanols / Q000737:chemistry*; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis*; D015394:Molecular Structure; D009947:Organotin Compounds / Q000737:chemistry*; D010618:Phenanthrolines / Q000138:chemical synthesis* / Q000737:chemistry; D010880:Piperidines / Q000737:chemistry; D011759:Pyrrolidines / Q000737:chemistry; D011807:Quinolizines / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D000440:Butanols; D007211:Indoles; D009947:Organotin Compounds; D010618:Phenanthrolines; D010880:Piperidines; D011759:Pyrrolidines; D011807:Quinolizines; C473343:antofine; C007160:cryptopleurine