Concise total syntheses of the Lycopodium alkaloids (+/-)-nankakurines A and B via luciduline.
Total syntheses of the Lycopodium alkaloids nankakurines A and B have been accomplished in 6 and 7 steps, respectively, via a sequence that passes through a third Lycopodium alkaloid, luciduline, and forgoes the use of protecting groups on nitrogen. Key features include a short preparation of luciduline followed by a concise and stereoselective aminoallylation/ring-closing metathesis protocol to fashion the spiropiperidine ring common to nankakurines A and B.
Cheng
Xiayun
X
Department of Chemistry, The University of Vermont, 82 University Place, Burlington, Vermont 05405, USA.
Waters
Stephen P
SP
D006572:Heterocyclic Compounds, Bridged-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011804:Quinolines / Q000737:chemistry*; D013237:Stereoisomerism
D006572:Heterocyclic Compounds, Bridged-Ring; D011804:Quinolines; C504053:nankakurine A; C547491:nankakurine B; C410447:luciduline