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InChI:InChI=1/C8H15NO/c10-6-7-3-5-9-4-1-2-8(7)9/h7-8,10H,1-6H2/t7-,8+/m1/s1

Upstream product

• 63527-07-1 1,8-H-trans-Pyrrolizidin-1-carbonsaeureethylester 
• 138947-27-0 (S)-1-Methylene-hexahydro-pyrrolizin-3-one 
• 112924-37-5 1-methyl-3-oxo-hexahydropyrrolizine 
• 78175-02-7 ethyl (-)-6β-hydroxy-8α-pyrrolizidine-1β-carboxylate 
• 85781-39-1 Acetic acid (1S,2S,7aS)-2-hydroxy-hexahydro-pyrrolizin-1-ylmethyl ester 
• 160024-31-7 (S)-7-methylenehexahydropyrrolizin-3-one 
• 194155-01-6 Methyl (2S)-1-(tert-butoxycarbonyl)-α-(prop-2-en-1-yl)pyrrolidine-2-acetate 
• 135081-79-7 (2S,βS)-1-(tert-Butoxycarbonyl)-β-(prop-2-en-1-yl)pyrrolidine-2-ethanol 
• 135081-82-2 (2S,γS)-1-(tert-Butoxycarbonyl)-γ-(tert-butyldimethylsilyloxymethyl)pyrrolidine-2-propanol 
• 135905-07-6 (2S,βS)-1-(tert-Butoxycarbonyl)-O-(tert-butyldimethylsilyl)-β-(prop-2-en-1-yl)pyrrolidine-2-ethanol 
• 135081-80-0 (S)-2-[(S)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-3-oxo-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 74046-07-4 (+)-Vigabatrin 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 69610-41-9 Boc-L-Pro-H 

Relevant academic research and scientific papers

Synthesis of the alkaloids (-)-heliotridane and (-)-isoretronecanol via π-allyltricarbonyliron lactam complexes

A novel synthesis of the pyrrolizidine alkaloids (-)-heliotridane (1) and (-)-isoretronecanol (2) is described. The key steps involve the conversion of a proline-derived carbamate (10) into the π-allyltricarbonyliron lactam complex (4) and the exhaustive carbonylation of this to give the pivotal intermediate γ-lactam (3). Lactam (3) has been converted into the title compounds by standard methods

Asymmetric syntheses of (-)-isoretronecanol and (-)-trachelantamidine

Short and concise total asymmetric syntheses of (-)-isoretronecanol and (-)-trachelantamidine are reported. Oxidative cleavage of tert-butyl (S,S,S,Z)-7-[N-benzyl-N-(α-methylbenzyl)amino]cyclohept-3-ene-1- carboxylate, followed by hydrogenolysis promoted

Stereodivergent Synthesis of 1-Hydroxymethylpyrrolizidine Alkaloids

A first stereodivergent strategy for the asymmetric synthesis of all stereoisomers of 1-hydroxymethylpyrrolizidine alkaloids is developed using an asymmetric self-Mannich reaction as a key step. An anti-selective self-Mannich reaction of methyl 4-oxobutanoate with the PMP-amine catalyzed by a chiral secondary amine is successfully optimized for the asymmetric synthesis of (+)-isoretronecanol and (-)-isoretronecanol. A syn-selective self-Mannich reaction catalyzed by proline is utilized for the asymmetric synthesis of the diastereomer, (+)-laburnine, and its enantiomer, (-)-trachelanthamidine.

ORGANIC REACTIONS

The present invention relates to various organic reactions including a method for producing heterocyclic compounds using a [3+2] annulation; a method for producing fluorinated heteroaromatic compounds; and a method for alkylating a meta-position of a phen

Asymmetric [3+2] Annulation Approach to 3-Pyrrolines: Concise Total Syntheses of (-)-Supinidine, (-)-Isoretronecanol, and (+)-Elacomine

An asymmetric [3+2] annulation reaction to form 3-pyrroline products is reported. Upon treatment with lithium diisopropylamide, readily available ethyl 4-bromocrotonate is deprotonated and trapped with Ellman imines selectively at the α-position to yield enantiopure 3-pyrroline products. This new method is compatible with aryl, alkyl, and vinyl imines. The efficacy of the method is showcased by short asymmetric total syntheses of (-)-supinidine, (-)-isoretronecanol, and (+)-elacomine. This novel annulation approach also works for an aldehyde, thus providing access to a 2,5-dihydrofuran product in a single step from simple precursors. By modifying the structure of the carbanion nucleophile, an asymmetric vinylogous aza-Darzens reaction can be realized.

Organocatalytic asymmetric mannich cyclization of hydroxylactams with acetals: Total syntheses of ( )-epilupinine, ( )-tashiromine, and ( )-trachelanthamidine

An asymmetric, organocatalytic, one-pot Mannich cyclization between a hydroxylactam and acetal is described to provide fused, bicyclic alkaloids bearing a bridgehead N atom. Both aliphatic and aromatic substrates were used in this transformation to furnish chiral pyrrolizidinone, indolizidinone, and quinolizidinone derivatives in up to 89% yield and 97% ee. The total syntheses of (-)-epilupinine, (-)-tashiromine, and (-)-trachelanthamidine also achieved to demonstrate the generality of the process.

Pyrrolizidine alkaloids from Liparis nervosa with inhibitory activities against LPS-induced NO production in RAW264.7 macrophages

Six pyrrolizidine alkaloids were isolated from the whole herb of Liparis nervosa together with two previously known ones. Their structures were elucidated by extensive spectroscopic analyses and chemical reactions. The cytotoxicity of the isolates was eva

Cremastrine, a pyrrolizidine alkaloid from Cremastra appendiculata

A new pyrrolizidine alkaloid, cremastrine (1), was isolated from the bulbs of Cremastra appendiculata. Its configuration was determined by spectroscopic and chemical analyses. Compound 1 inhibited the binding of tritium-labeled N-methylscopolamine to the muscarinic M3 receptor with a Ki value of 126 nM.

Highly efficient and stereoselective radical addition of tertiary amines to electron-deficient alkenes - Application to the enantioselective synthesis of necine bases

A convenient and highly efficient method for the regio- and stereoselective addition of tertiary amines to electron-deficient alkenes has been elaborated. It is based on a radical chain reaction of α-aminyl radicals with alkenes, induced by a photoelectro

Enamino ester reduction: A short enantioselective route to pyrrolizidine and indolizidine alkaloids. Synthesis of (+)-laburnine, (+)-tashiromine, and (-)-isoretronecanol

Various chiral pyrrolidine tetrasubstituted β-enamino esters were reduced catalytically or chemically with good to moderate diastereoselectivity owing to a chiral induction originated from (S)-α- methylbenzylamine. With endocyclic double bond compounds, t