551-59-7

Usage

InChI:InChI=1/C8H13NO/c10-6-7-3-5-9-4-1-2-8(7)9/h3,8,10H,1-2,4-6H2/t8-/m0/s1

Upstream product

• 138478-74-7 (8S)-O-Benzylsupinidine 
• 78175-02-7 ethyl (-)-6β-hydroxy-8α-pyrrolizidine-1β-carboxylate 
• 122695-55-0 Acetic acid 2-(2-hydroxy-5-oxo-pyrrolidin-1-yl)-ethyl ester 
• 122744-13-2 5(S)-1-aza-4-(acetoxymethyl)bicyclo<3.3.0>oct-3-en-8-one 
• 520-63-8 (+)-heliotridine 
• 126191-54-6 7-O-(Phenoxythiocarbonyl)-9-O-benzoylheliotridine 
• 126191-52-4 7-O-(Phenoxythiocarbonyl)-9-O-(tert-butyldimethylsilyl)heliotridine 
• 126191-51-3 9-O-Benzoylheliotridine 
• 126253-89-2 9-O-(tert-Butyldimethylsilyl)heliotridine 
• 122695-49-2 3-(2-(1-(2-acetoxyethyl)-5-oxo-2-pyrrolidinyl)(phenylthio)acetyl)-4(R)-isopropyl-1,3-thiazolidine-2-thione 
• 122695-48-1 [(S)-1-(2-Methanesulfonyloxy-ethyl)-5-oxo-pyrrolidin-2-yl]-phenylsulfanyl-acetic acid methyl ester 
• 122695-54-9 methyl 2(RS)-(1-(2-iodoethyl)-5-oxo-2(S)-pyrrolidinyl)(phenylthio)acetate 
• 122695-50-5 methyl 2(RS)-1-(1-(2-hydroxyethyl)-5-oxo-2(S)-pyrrolidinyl)(phenylthio)acetate 
• 132288-57-4 (4R,5S)-1-aza-4-phenylthio-4-(methoxycarbonyl)bicyclo<3.3.0>octan-8-one 

Downstream Products

• 526-63-6 (-)-isoretronecanol 

Relevant academic research and scientific papers

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.

A synthesis of (-) supinidine and its regioisomer by intramolecular oxime olefin cycloaddition

A synthesis of (-)supinidine 1 and its regioisomer 2 from L-proline is described. The key step is a thermal intramolecular oxime-olefin cycloaddition; dimerization products resulting from intramolecular nitrone formation were also isolated.

AN ASYMMETRIC TOTAL SYNTHESIS OF (-)-SUPINIDINE

By starting from the N-alkenylurethane 4, the epoxy urethane ent-5, and the pyrrolidine ent-6 available from the Katsuki-Sharpless kinetic resolution of N-benzyloxycarbonyl-3-hydroxy-1-pentenylamine (2) has been elaborated (-)-supinidine (1). Key Words: K

DIASTEREOSELECTIVE ALKYLATION OF CHIRAL TIN(II) ENOLATES ONTO CYCLIC ACYL IMINIUM IONS. ASYMMETRIC TOTAL SYNTHESIS OF (-)-SUPINIDINE

The scope and mechanism of the asymmetric alkylation of chiral tin(II) enolate 10 with cyclic acyl iminium ion 5 were investigated.An application of the reaction to the asymmetric synthesis of (-)-supinidine was also achieved.

NEW CHIRAL RECOGNITION OF CHIRAL TIN(II) ENOLATES TOWARD CYCLIC ACYL IMINIUM SPECIES. ASYMMETRIC TOTAL SYNTHESIS OF (-)-SUPINIDINE

Diastereoselective alkylation of chiral tin(II) enolates 1 onto cyclic acyl iminium ion 7 proceeded in a different chiral recognition mode from the case of 1 onto cyclic acyl imines 3.This new diastereoselective alkylation was efficiently utilized for an asymmetric total synthesis of (-)-supinidine (20).

THE SYNTHESIS OF (-)-ISORETRONECANOL, (-)-TRACHELANTHAMIDINE, AND (-)-SUPINIDINE FROM (S)-PROLINE

Dieckmann cyclisation of (S)-N,2-di(carboethoxymethyl)pyrrolidine, made from (S)-proline, gave (8S)-1-carboethoxypyrrolizidin-2-one, which was then converted into (-)-isoretronecanol, (-)-trachelanthamidine, and (-)-supinidine.

Synthesis of Optically Active Pyrrolizidine Bases

Regiospecific 1,3-dipolar cycloaddition of ethyl propiolate to the NO-diformyl derivative (1) of natural (-)-4-hydroxy-L-proline followed by stereospecific hydrogenation gave ethyl (+)-6α-hydroxy-β-pyrrolizidine-1α-carboxylate (4).Confirmation of the abso