98482-33-8

Upstream product

• 130581-87-2 (R)-methyl 2-(benzyloxycarbonylamino)-5-(tert-butoxycarbonylamino)pentanoate 
• 725250-71-5 (1R)-(9aR)-octahydro-quinolizine-1-carboxylic acid methyl ester 

Downstream Products

• 1004-90-6 norlupinene 
• 10447-19-5 (9aR)-(9ar)-octahydro-quinolizin-1ξ-ol 

Relevant academic research and scientific papers

Stereoflexible total synthesis of (-)-epiquinamide

Hydroxy propiolate rearrangement to conjugated diene, Sharpless asymmetric dihydroxylation and one-pot quinolizine construction have been used as key steps in the total synthesis of (-)-epiquinamide.

Divergent method to trans -5-hydroxy-6-alkynyl/alkenyl-2-piperidinones: Syntheses of (-)-epiquinamide and (+)-swainsonine

An efficient diastereoselective approach to access trans-5-hydroxy-6-alkynyl/alkenyl-2-piperidinones has been developed through nucleophilic addition of α-chiral aldimines using alkynyl/alkenyl Grignard reagents. The diastereoselectivity of alkenyl in C-6

A hydrozirconation/iodination-mediated access to tetrahydroquinolizinium salts. Application to the synthesis of Lupinine and (-)-Epiquinamide

The preparation of tetrahydroquinolizinium salts, based on a hydrozirconation/iodination sequence involving 2-pyridyl alkenes, is presented. This approach was applied to the synthesis of substituted quinolizines as illustrated by the synthesis of Lupinine

Short total synthesis of (-)-lupinine and (-)-epiquinamide by double Mitsunobu reaction

Alternative total syntheses of (-)-lupinine (1) and (-)-epiquinamide (2) have been described via the key intermediate 3 obtained from the addition of 2-trialkylsilyloxyfuran 5 to N-acyliminium intermediate derived from 4. The major R,R-isomer 8 obtained from the Mannich reaction was converted into its R,S-isomer through Mitsunobu reaction. Then, a second Mitsunobu reaction of 3 led to cyano 9 and azido 11 derivatives, which were converted into 1 and 2 in 33 and 36% overall yield from 4, respectively. The synthetic route is amenable for the generation of several quinolizidine alkaloids. Georg Thieme Verlag Stuttgart · New York.

Epiquinamide: A Poison That Wasn't from a Frog That Was

In 2003, we reported the isolation, structure elucidation, and pharmacology of epiquinamide (1), a novel alkaloid isolated from an Ecuadoran poison frog, Epipedobates tricolor. Since then, several groups, including ours, have undertaken synthetic efforts to produce this compound, which appeared initially to be a novel, β2-selective nicotinic acetylcholine receptor agonist. Based on prior chiral GC analysis of synthetic and natural samples, the absolute structure of this alkaloid was established as (15,9aS)-1-acetamidoquinolizidine. We have synthesized the (1.R*,9aS*)-isomer (epiepiquinamide) using an iminium ion nitroaldol reaction as the key step. We have also synthesized ent-1 semisynthetically from (-)-lupinine. Synthetic epiquinamide is inactive at nicotinic receptors, in accord with recently published reports. We have determined that the activity initially reported is due to cross-contamination from co-occurring epibatidine in the isolated material.

Practical total syntheses of epiquinamide enantiomers

Short and practical syntheses of epiquinamide and its enantiomer were accomplished with high overall yields and high stereoselectivity from readily available starting materials. American Chemical Society.