90-39-1

Usage

Uses

Used in Pharmaceutical Industry:
(-)-SPARTEINE is used as an oxytocic agent for its ability to stimulate the contraction of smooth muscles, particularly in the uterus. This property makes it valuable in the management of certain obstetric conditions, such as facilitating childbirth or controlling postpartum bleeding.

Health Hazard

Toxic actions of sparteine are similar to thoseof coniine but are much less toxic than thoseof coniine. The toxic symptoms in mice weretremor, muscle contraction, and respiratorydistress. An intraperitoneal dose lethal toguinea pigs is 23 mg/kg.LD50 value, oral (mice): 220 mg/kg.

InChI:InChI=1/C15H26N2/c1-3-7-16-11-13-9-12(14(16)5-1)10-17-8-4-2-6-15(13)17/h12-15H,1-11H2/t12-,13-,14-,15+/m1/s1

Upstream product

• 299-39-8 (-)-sparteine; bis-hydrogen sulfate 
• 2739-98-2 ethyl 2-(pyridinyl-2)acetate 
• 773070-58-9 ethyl {(2S)-1-[(1R)-1-phenylethyl]piperidin-2-yl}acetate 
• 489-54-3 (1R,2R,9S,10S)-7,15-diazatetracyclo[7.7.1.0^2,7.0^10,15]heptadecane-8,16-dione 
• 550-90-3 (+)-lupanine 
• 90-39-1 (+-)-sparteine 
• 1476-39-7 1,5-diaminopentane dihydrochloride 
• 72074-77-2 d,l-lupanine 
• 505-18-0 2,3,4,5-tetrahydropyridine 

Downstream Products

• 489-72-5 (-)-17-oxosparteine 
• 477-22-5 (7S,7'R)-(7at,7'ac',14'at')-Δ^1(14a)-docosahydro-7r,14c;7'r',14'c'-dimethano-[1,6'ξ]bi[dipyrido[1,2-a;1',2'-e][1,5]diazocinyl] 
• 489-72-5 17-oxosparteine 
• 486-87-3 (-)-(6S,7R,9R,11R)-lupanine 
• 82263-24-9 (+)-6-benzylsparteine 
• 549503-58-4 2-(2-fluorophenyl)-1-methylethyl diisopropylcarbamate 
• 152857-74-4 (R)-(+)-[1-Benzyl-3-(N,N-dibenzylamino)-propyl] 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate 
• 2130-67-8 (+/-)-(14at)-1,3,4,7,9,10,11,13,14,14a-decahydro-2H,6H-7r,14c-methano-dipyrido[1,2-a;1',2'-e][1,5]diazocine 

Relevant academic research and scientific papers

ALKALOID DISTRIBUTION IN SOME SPECIES OF THE PAPILIONACEOUS TRIBES SOPHOREAE, DALBERGIEAE, LOTEAE, BRONGNIARTIEAE AND BOSSIAEEAE

Quinolizidine and dipiperidine alkaloid profiles have been determined for various plant parts of ten papilionaceous species in the tribes Sophoreae, Dalbergieae, Brongniartieae and Bossiaeeae.Alkaloids have been identified for the first time from species in the tribes Dalbergieae (Dalbergia monetaria) and Brongniartieae (Harpalyce formosa var. formosa) of Polhill's classification system of the Papilionoideae.No alkaloids were detected in seeds of several Lotus species (tribe Loteae).Quinolizidine-indolizidine alkaloids of the leontidine type, including 11-epileontidane, a new compound, were obtained from the leaves and stems of Maackia amurensis. 11,12-Dehydrosparteine, a compound which has not previously been characterized as a natural product, was observed in an extract of the stems of Templetonia egena. - Key Word Index - Papilionoideae; tribes Sophoreae, Dalbergieae, Loteae, Brongniartieae, Bossiaeeae; Leguminosae; chemotaxonomy; quinolizidine alkaloids; 11-epileontidane; 11,12-dehydrosparteine.

Gram-Scale Synthesis of the (?)-Sparteine Surrogate and (?)-Sparteine

An 8-step, gram-scale synthesis of the (?)-sparteine surrogate (22 % yield, with just 3 chromatographic purifications) and a 10-step, gram-scale synthesis of (?)-sparteine (31 % yield) are reported. Both syntheses proceed with complete diastereocontrol and allow access to either antipode. Since the syntheses do not rely on natural product extraction, our work addresses long-term supply issues relating to these widely used chiral ligands.

The Enantioselective Total Synthesis of Bisquinolizidine Alkaloids: A Modular “Inside-Out” Approach

Bisquinolizidine alkaloids are characterized by a chiral bispidine core (3,7-diazabicyclo[3.3.1]nonane) to which combinations of an α,N-fused 2-pyridone, an endo- or exo-α,N-annulated piperidin(on)e, and an exo-allyl substituent are attached. We developed a modular “inside-out” approach that permits access to most members of this class. Its applicability was proven in the asymmetric synthesis of 21 natural bisquinolizidine alkaloids, among them more than ten first enantioselective total syntheses. Key steps are the first successful preparation of both enantiomers of C2-symmetric 2,6-dioxobispidine by desymmetrization of a 2,4,6,8-tetraoxo precursor, the construction of the α,N-fused 2-pyridone by using an enamine-bromoacrylic acid strategy, and the installation of endo- or, optionally, exo-annulated piperidin(on)es.

A Two-Directional Synthesis of (+)-β-Isosparteine

A two-directional synthesis of (+)-β-isosparteine is described in five steps from glutaric acid, where the entire carbon and nitrogen backbone of the alkaloid, possessing the requisite relative and absolute stereochemistry at its four stereogenic centers, is assembled using a double imino-aldol reaction.

PROCESS FOR CONVERTING LUPANINE INTO SPARTEINE

The present invention relates to processes for preparing enantiopure Lupanine and Sparteine.

Simple and highly efficient preparation and characterization of (-)-lupanine and (+)-sparteine

In a simple and convenient way, we have improved the non-chromatographic isolation of optically pure (-)-2-oxosparteine ((-)-lupanine) and (+)-sparteine. The fast and efficient method for the determination of the ee of bisquinolizidine alkaloids has been proposed. A relatively simple simple 1H NMR method has been applied for evaluation of the % ee of enantiomers of the lupanines and sparteines with the chiral dibenzoyltartaric acids as the shift reagents. The 1H NMR spectra of the bases and the new salts in polar solvents have been measured. The results are confirmed by chiral HPLC method. Additionally, for the first time X-ray analysis of the salt of (-)-lupanine has been performed. The improved method of purification of bisquinolizidine alkaloids will considerably facilitate the employment of these alkaloids as chiral ligands in asymmetric reactions and as pharmacological tools.

Concise asymmetric synthesis of (-)-sparteine

A six-step asymmetric synthesis of natural (-)-sparteine from ethyl 7-iodohept-2-enoate is reported, involving a connective Michael addition of an amino ester-derived enolate to an α,β-unsaturated amino ester.

Oxidative deamination of tetrahydroanabasine with o-quinones: An easy entry to lupinine, sparteine, and anabasine

A mild oxidative deamination reaction of tetrahydroanabasine O-methyloxime 17 is described, making use of an o-quinone that is based on topaquinone (TPQ, 11), the cofactor that is present in copper-containing amine oxidases. In situ ring closure of the oxidation product produced double functionalized quinolizidine 5, containing an enamine functionality with excellent reactivity. From this quinolizidine 5 a variety of biogenetically related lupin alkaloids were prepared: lupinine (7) and aminolupinane (8) via reductive sequences and sparteine (9) via a condensation reaction with dehydropiperidine 1. The configurationally more favorable trans isomers epilupinine (25) and β-isosparteine (10) were formed when more drastic reaction conditions were used for oxime hydrolysis. Anabasine (4) and a new 5-piperidylanabasine derivative 6 were formed by an unexpected acid catalyzed ring transformation reaction, whereby the pyridine ring was formed via oxime-induced aromatization. The stereochemistry of the reaction products and the biogenetic implications are discussed.

Synthesis of Cadaverine and its Incorporation into five Quinolizidine Alkaloids

Cadaverine dihydrochloride (13) was synthesised by the sequential introduction of two equivalents of sodium cyanide to a C3 precursor, and it was fed to Lupinus luteus and L. polyphyllus plants.Complete labelling patterns were obtained in five quinolizidine alkaloids by 13C n.m.r. spectroscopy.The 13C-13C doublets observed in the spectra of (-)-lupinine (3), (-)-sparteine (4), (+)-lupanine (5), (+)-13α-hydroxylupanine (6), and (+)-angustifoline (7) derived biosynthetically from the doubly labelled precursor (13) confirm the intact, specific incorporation of two cadaverine units into the tetracyclic quinolizidine alkaloid skeletons.The cadaverine (13) units are incorporated to about the same extent into each part of the quinolizidine alkaloids (3)-(7).Two of the 13C chemical shifts for lupanine (5) have been reassigned.The labelling pattern of the tricyclic alkaloid angustifoline (7) indicates that the allyl group originates by degradation of one ring of a tetracyclic precursor.