title: Total synthesis of (-)-lycoperine A.
abstract: 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.
authors: Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, California 92697-2025, USA.
authors: Yoshitaka
authors: Y
authors: Nakamura
authors: Anthony M
authors: AM
authors: Burke
authors: Shunsuke
authors: S
authors: Kotani
authors: Joseph W
authors: JW
authors: Ziller
authors: Scott D
authors: SD
authors: Rychnovsky
mesh_terms: 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
chemical_list: D000470:Alkaloids; D011804:Quinolines; C507691:lycoperine A