Total synthesis of (-)-lycoperine A.
Lycoperine A was synthesized through a highly convergent route in which a double alkylation of 2,6-dicyano-N-benzylpiperidine with the octahydroquinoline moiety gave the lycoperine skeleton. The octahydroquinoline was prepared by a desymmetrization reaction of 5-methylcyclohexane-1,3-dione. Hydrolysis, reductive amination, and cyclization gave lycoperine A in 13 steps and 3% overall yield. The absolute configuration of lycoperine A was assigned as 6R,6'R,8R,8'R,13S,17R.
Nakamura
Yoshitaka
Y
Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, California 92697-2025, USA.
Burke
Anthony M
AM
Kotani
Shunsuke
S
Ziller
Joseph W
JW
Rychnovsky
Scott D
SD
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000493:pharmacokinetics*; D000478:Alkylation; D003500:Cyclization; D032502:Lycopodium / Q000737:chemistry; D015394:Molecular Structure; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D011804:Quinolines; C507691:lycoperine A