7773-46-8

Upstream product

• 103833-63-2 8-Methyl-2-phenyl-hexahydro-isoxazolo[2,3-a]pyridin-8-ium; iodide 
• 101113-68-2 (+/-)-sedaminone 
• 110-89-4 piperidine 
• 1796-27-6 piperidine-1-carboxylic acid methyl ester 
• 56475-86-6 2-methoxy-piperidine-1-carboxylic acid methyl ester 
• 138371-96-7 tert-butyl 2-(2-oxo-2-phenylethyl)piperidine-1-carboxylate 
• 536-74-3 phenylacetylene 
• 91951-58-5 tert-butyl (tetrahydro-2H-pyran-2-yl)carbamate 
• 138371-93-4 (1SR,2SR) N-ethoxycarbonyl-2-(β-hydroxy-β-phenylethyl)piperidine 
• 70546-72-4 (2S,3aR)-8-Methyl-2-phenyl-hexahydro-isoxazolo[2,3-a]pyridin-8-ium; iodide 
• 70546-72-4 (2R,3aR)-8-Methyl-2-phenyl-hexahydro-isoxazolo[2,3-a]pyridin-8-ium; iodide 
• 50-00-0 formaldehyd 
• 495-47-6 (±)-norsedamine 
• 79-22-1 methyl chloroformate 

Downstream Products

• 70561-76-1 (±)-allosedamine 
• 67008-23-5 (2R)-2-((2R)-2-hydroxy-2-phenylethyl)-1-methylpiperidine 
• 497-88-1 (-)-sedamine 

Relevant academic research and scientific papers

Synthesis of a 3,4-Dihydro-1,3-oxazin-2-ones Skeleton via an Intermolecular [4 + 2] Process of N-Acyliminium Ions with Ynamides/Terminal Alkynes

An approach to access functionalized 3,4-dihydro-1,3-oxazin-2-ones has been developed by reacting semicyclic N,O-acetals 5 and 6 with ynamides 7 or terminal alkynes 8 in a one-pot fashion. The reaction went through a formal [4 + 2] cycloaddition process to generate a number of functionalized 3,4-dihydro-1,3-oxazin-2-ones 9a-9ak and 10a-10bc in yields of 34-97%. In addition, the utility of this transformation was demonstrated by the synthesis of (±)-sedamine 13.

Decarboxylative Conjunctive Cross-coupling of Vinyl Boronic Esters using Metallaphotoredox Catalysis

The synthesis of complex alkyl boronic esters through conjunctive cross-coupling of vinyl boronic esters with carboxylic acids and aryl iodides is described. The reaction proceeds under mild metallaphotoredox conditions and involves an unprecedented decarboxylative radical addition/cross-coupling cascade of vinyl boronic esters. Excellent functional-group tolerance is displayed, and application of a range of carboxylic acids, including secondary α-amino acids, and aryl iodides provides efficient access to highly functionalized alkyl boronic esters. The decarboxylative conjunctive cross-coupling was also applied to the synthesis of sedum alkaloids.

A rapid access to (±)-sedamine and some original N -benzyl unsaturated analogues

Reduction of N-alkyl-2-(2-hydroxy-2-phenylethyl)pyridinium salts using excess of sodium triacetoxyborohydride afforded exclusively the corresponding tetrahydropyridine derivative bearing a piperidine ring with a double bond in the 3,4-position. Furthermore, under these conditions, syn-1,3-amino alcohols were obtained in good yield and diastereoselectivity. Georg Thieme Verlag Stuttgart · New York.

Hydroformylation of homoallylic azides: A rapid approach toward alkaloids

(Chemical Equation Presented) Unprecedented hydroformylation of homoallylic azides combined with useful one-pot operations provides an expeditive access to alkaloids.

Enantioselective synthesis of lobeline via nonenzymatic desymmetrization

Lobeline has been prepared in enantiopure form via desymmetrization of lobelanidine with use of BTM, a nonenzymatic enantioselective acyl transfer catalyst.

A concise synthesis of homochiral sedamines and related alkaloids. A new reductive application of Jacobsen's catalyst

Two methods for the generation of both enantiomers of sedamine [1- methyl-2-(2-phenyl-2-hydroxy-1-ethyl)piperidine] in high optical purity have been elaborated. The first utilises the lipase-mediated kinetic resolution of racemic acetates and the second involves the NaBH4 mediated reduction of ketones catalysed by Jacobsen's catalyst. Some related applications of these reactions are also disclosed.

ALKALOIDS OF SOME EUROPEAN AND MACARONESIAN SEDOIDEAE AND SEMPERVIVOIDEAE (CRASSULACEAE)

Some 22 pyrrolidine and piperidine alkaloids were detected in the leafy parts of Sedum acre, S. aetnense, S. anglicum, S. brissemoreti, S. farinosum, S. fusiforme, S. lancerottense, S. melanantherum, and S. nudum.In addition to the alkaloids known from S. acre, 1-(2-pyrrolidyl)-propan-2-one and 2-monosubstituted piperidine alkaloids bearing butan-2-one, butan-2-ol, pentan-2-one and pentan-2-ol sidechains were identified.Phenylethylamine was isolated from the vegetative parts of S. album.In S. lydium, S. meyeri-johannis, and 16 species of S. series Rupestria, Aeonium, Greenovia, Jovibarba and Sempervivum no alkaloids could be detected.The results indicate a correlation between the presence of alkaloids and the major evolutionary trends in the European and Macaronesian Crassulaceae. Key Word Index: Sedum; Aeonium; Greenovia; Jovibarba; Sempervivum; Crassulaceae; pyrrolidine and piperidine alkaloids; chemotaxonomy; evolution.

A FACILE SYNTHESIS OF dl-SEDAMINE AND dl-ALLOSEDAMINE

Racemic sedamine and dl-allosedamine were easily synthesized from the intermediate (3) using a cyclic acyliminium salt by the addition-elimination reaction sequence.

Trimethylsilyl trifluoromethanesulfonate (TMSOTf) catalyzed amidoalkylation of silylenolethers. Stereocontrolled syntheses of (+/-)-sedamine and (+/-)-norsedamine

Trimethylsilyl trifluoromethanesulfonate (TMSOTf) catalyzed addition of 1-trimethylsilyloxy-1-phenylethene to N-ethoxycarbonyl- and N-tert-butoxycarbonyl-2-ethoxypiperidines (3a and 3b, respectively) afforded the corresponding ketocarbamates 4a and 4b, in excellent yields. Stereoselective conversion to (±)-norsedamine (7) and (±)-sedamine (8) is described.