38142-93-7

Upstream product

• 1042150-18-4 (R)-methyl 3-(4-methyl-6-oxocyclohex-1-enyl)propanoate 
• 92597-46-1 (4aα,5α,7β,8aα)-Decahydro-1,7-dimethyl-2-oxo-5-chinolinessigsaeure-methylester 
• 83532-71-2 7-Methyl-2,3,4,6,7,8-hexahydroquinoline 
• 92597-42-7 (4aα,5α,7β,8aα)-Decahydro-1,7-dimethyl-5-chinolinessigsaeure-methylester 
• 92597-49-4 trans-5,6,7,8-Tetrahydro-7-methyl-5-chinolinessigsaeure-methylester 
• 50-00-0 formaldehyd 
• 92597-53-0 (E/Z)-5,6,7,8-Tetrahydro-7-methyl-5-chinolinylidenessigsaeure-ethylester 
• 92597-52-9 [7-Methyl-7,8-dihydro-6H-quinolin-(5Z)-ylidene]-acetic acid methyl ester 

Relevant academic research and scientific papers

Studies on the Synthesis of Phlegmarine-Type Lycopodium Alkaloids: Enantioselective Synthesis of (-)-Cermizine B, (+)-Serratezomine E, and (+)-Luciduline

The synthesis of the Lycopodium alkaloids, (-)-cermizine B, (+)-serratezomine E, and (+)-luciduline using phenylglycinol-derived tricyclic lactams as chiral scaffolds, is reported. The requisite lactams are prepared by a cyclocondensation reaction between (R)- or (S)-phenylglycinol and the substituted δ-keto ester 11, easily accessible from (R)-pulegone. The factors governing the stereoselectivity of these cyclocondensation reactions are discussed. Key steps of the synthesis from the stereochemical standpoint are the stereoselective elaboration of the allyl substituent to the (S)-2-(piperidyl)methyl moiety and the stereoselective removal of the chiral inductor to give a cis-decahydroquinoline.

Concise total syntheses of the lycopodium alkaloids (±)-nankakurines A and B via luciduline

(Figure presented) 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 luclduline followed by a concise and stereoselective amlnoallylatlon/ring-closlng metathesis protocol to fashion the spiropiperidine ring common to nankakurines A and B.

Synthesis of the Lycopodium Alkaloid rac-Luciduline from Hexahydro-7-methylquinoline

The 1,4 addition of malonic acid to the eneimine functional group of 2 leads to diastereomeric imines which via disproportionation can be transformed into the pyridine derivative 9.From 9 the ester 5b is obtained stereoselectively.Oxidation of 5b with potassium permanganate and crown ether yields the lactam ester 15.The cyclization and transformation of 15 into rac-luciduline (1) is described. 5b can also be obtained in a simple, nonstereoselective synthesis from the ketone 10.