72203-34-0

Upstream product

• 67-56-1 methanol 
• 934-30-5 5-norbornene-endo-2-carboxylic acid 
• 186581-53-3 diazomethane 
• 120-74-1 (1R,2R)-5-norbornene-2-carboxylic acid 
• 120-74-1 (1R,2S)-5-norbornene-2-carboxylic acid 
• 192130-82-8 (3S,8aR)-3-Benzyl-2-((1R,2R,4R)-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-hexahydro-pyrrolo[1,2-a]pyrazine-1,4-dione 
• 124-41-4 sodium methylate 
• 136520-58-6 methyl (5R,6R)-6-endo-formylbicyclo<2.2.1>hept-2-eno-5-exo-carboxylate 
• 136520-59-7 methyl (5R,6R)-5-exo-formylbicyclo<2.2.1>hept-2-eno-6-endo-carboxylate 
• 120-74-1 (-)-(1S,4S,5R)-bicyclo<2.2.1>hept-2-ene-5-carboxylic acid 
• 120-74-1 (1S,2S,4S)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid 

Downstream Products

• 1610892-37-9 C₁₆H₁₈O 
• 344585-18-8 (1S,2S,4R)-2-Isocyanato-bicyclo[2.2.1]heptane 
• 120-74-1 (+)-(1R,4R,5S)-bicyclo<2.2.1>hept-2-ene-5-carboxylic acid 
• 822-98-0 (1R,2R,4S)-bicyclo[2.2.1]hept-2-ylamine 
• 84235-33-6 (+)-(1S,2S,4R)-2-norbornylamine 
• 120-74-1 (-)-(1S,4S,5R)-bicyclo<2.2.1>hept-2-ene-5-carboxylic acid 
• 344585-18-8 (1R,2R,4S)-2-Isocyanato-bicyclo[2.2.1]heptane 

Relevant academic research and scientific papers

2,5-diketopiperazines, new chiral auxiliaries for asymmetric Diels-Alder reactions

Diketopiperazines have been utilized as chiral auxiliaries for asymmetric Diels-Alder reactions. Cyclo-S-phenylalanyl-R-proline (2) was found to be the most promising of these auxiliaries and afforded Diels-Alder adducts in high chemical yield (78-95%), with endo selectivities generally greater than 9:1. The diastereoselectivities observed were comparable to the best previously published values.

Novel Potassium-Channel Openers: Preparation and Pharmacological Evaluation of Racemic and Optically Active N-(6-Amino-3-pyridyl)-N'-bicycloalkyl-N"-cyanoguanidine Derivatives

The previous paper reported on the synthesis and pharmacological evaluation of N-(6-amino-3-pyridyl)-N'-bicycloalkyl-N"-cyanoguanidine derivatives, from among which three compounds were selected as potent potassium-channel openers. In the present study, selected compounds were tested for antagonism of potassium-induced contraction of rat aorta, hypotensive activity in normotensive rats, and diuretic activity in spontaneously hypertensive rats. This led to further evaluation of compound (+/-)-10 and selection of (+)-N-(6-amino-3-pyridyl)-N'-hept-2-yl>-N"-cyanoguanidine ((+)-10) (AL0670) for development as an antihypertensive agent. Although AL0670 is regarded as a pinacidil-type K+-channel opener, it showed different pharmacological and conformational profiles from pinacidil.

Stereoselection in Thermal Asymmetric Diels-Alder Reactions. Electronic vs Steric Effects

Experimental evidence was found for an electronic contribution favoring the cisoid conformation of α,β-unsaturated carbonyl compounds in thermal Diels-Alder transition states.

Transformations of unsaturated acyclic sugars into enantiomerically pure norbornene derivatives

The C7 acyclic unsaturated-sugar ester 1, derived from L-arabinose, and its enantiomer serve as convenient dieneophiles for chirality transfer for synthesis of optically pure carbocyclic derivatives through cycloaddition reactions.Reaction of 1 with cyclopentadiene may be controlled to give preparative access to the 5,6-disubstituted norbornene adducts 4a, 5a and 7a, according to the conditions used.The distribution of the four possible isomeric products from this cycloaddition was quantitated, and the effect of substitutional variation on the precursor dienophile 1 was also examined.Adducts 4a and 5a were transformed into such substituted carbocycles of known absolute configuration as the methyl esters (11 and 12) of norbornene (bicyclohept-2-ene)-6-carboxylic acid and nortricyclane (tricyclo2,6>heptane)-3-carboxylic acid in optically pure form, specifically through decarbonylation reactions using RhCl(PPh3)3 (Wilkinson's complex) and Cl.The optical purity of 12 was established by the use of a chiral lanthanide shift-reagent.

Asymmetric Diels-Alder Reaction Using (S)-Pyroglutamic Acid Derivatives as Chiral Dienophiles

Asymmetric Diels-Alder reaction of cyclopentadiene with chiral dienophiles (3) derived from (S)-pyroglutamic acid derivatives was performed in the presence of a Lewis acid such as diethylaluminium chloride in toluene to afford the cycloadducts with high diastereoselectivity.Keywords asymmetric reaction; Diels-Alder reaction; (S)-pyroglutamic acid; chiral dienophile; diethylaluminium chloride; (2+4)cycloaddition

Diels-Alder Reaction of Chiral Acrylamide and a Convenient Synthesis of Optically Pure Methyl (3R, 4R, 6R)-Bicycloheptene-4-carboxylate

Asymmetric Diels-Alder reaction of the chiral acrylamide 1 proceeds highly diastereoselectively and methanolysis of the adduct 2 gives the optically pure (3R, 4R, 6R)-bicycloheptene-4-carboxylate.

INFLUENCE OF POLAR GROUPS IN THERMAL AND LEWIS ACID PROMOTED ASYMMETRIC DIELS-ALDER ADDITIONS: LACTIC ACID DERIVATIVES AS PRACTICAL HIGHLY SELECTIVE AND CONFIGURATIONALLY DICHOTOMIC REAGENTS

Diels-Alder reactions of the acrylate of (S)-ethyl lactate with cyclopentadiene proceed with diastereoface-selectivity of up to 85:15 (non catalyzed) and 93:7 (TiCl4-promoted).Depending on the Lewis acid, products of inverse configuration are obtained.In conjunction with facile product analysis by LC, effective means for suppression of the polymerization of diene, and virtually epimerization-free ester hydrolysis these findings constitute a method for large scale practical applications of the asymmetric Diels-Alder reaction.