103233-14-3Relevant academic research and scientific papers
Stereospecificity in Allergic Contact Dermatitis to Simple Substituted Methylene Lactone Derivatives
Mattes, Henri,Hamada, Kaoru,Benezra, Claude
, p. 1948 - 1951 (1987)
The enantiomers of β,γ-dimethyl- and β-methyl-α-methylene-γ-butyrolactones have been synthesized stereospecifically from glutamic acid and β-hydroxy isobutyric acid, respectively.Guinea pigs have been sensitized (Freund complete adjuvant technique) and tested to them.Both enantiomers of β-methyl lactone as well as (+)-β,γ-dimethyl lactone induced enantiospecific allergic contact dermatitis (ACD); in turn, (-)-β,γ-dimethyl lactone showed no specificity.An interpretation is proposed.
Stereoselective Construction of the Methylcyclopentane Core of Peditithins B-H with Five Continuous Stereocenters
Li, Qingjiang,Li, Wei,Ni, Fu-Qiang,Wu, Shu-Qi,Yin, Sheng
, p. 9360 - 9364 (2020)
A stereoselective construction of the methylcyclopentane core (3) of jatrophane diterpenoids peditithins B-H was achieved in 14 steps from commercially available d-(+)-ribono-1,4-lactone (9). The linear 5-ene-heptanal derived from 9 was cyclized to the five-membered ring by an intramolecular carbonyl ene reaction, and five continuous stereocenters on 3 were stereoselectively introduced via a successive substrate-controlled manner, involving diastereoselective 1,4-addition, MoOPH-induced hydroxylation, and stereospecific epoxidation.
Novel Bicyclic Pyridinones
-
Page/Page column, (2014/04/03)
Compounds and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of Formula I as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed.
Synthetic study on gymnodimine: Highly stereoselective construction of substituted tetrahydrofuran and cyclohexene moieties
Ishihara, Jun,Miyakawa, Jun,Tsujimoto, Takashi,Murai, Akio
, p. 1417 - 1419 (2007/10/03)
The synthetic studies on gymnodimine, a shellfish toxin, are described. This marine toxin consists of 16-membered carbocycle, tetrahydrofuran, and spiro-imine moieties. Our synthetic strategy involves the stereoselective allylation of tetrahydrofuran compound and the exo-selective intramolecular Diels-Alder reaction.
Synthesis of γ-lactone derivatives as a key intermediate for the spiroketal fragment in calyculin A
Kabeya, Mototsugu,Hamada, Yasumasa,Shioiri, Takayuki
, p. 9769 - 9776 (2007/10/03)
A simple and safe route to the D-xylone-l,4-lactone derivative 3, a key intermediate for the synthesis of the spiroketal fragment in calyculin A (I) has been explored without the use of hazardous diazomethane on a large scale.
A synthetic route to 3-C-alkyl (or 3-C-phenyl-) 2,3-dideoxy-D-erythro- pentono-1,4-lactones: Intermediates in the synthesis of 2(3H)-furanones
Raveendranath,Blazis,Agyei-Aye,Hebbler,Gentile,Hawkins,Johnson,Baker
, p. 207 - 223 (2007/10/02)
A series of 3-C-alkyl- (and 3-C-phenyl-) 2,3-dideoxy-D-erythro-pentono- 1,4-lactones, compounds which are important in the synthesis of modified nucleosides and antibiotic sugars, were synthesized from D-ribonolactone. By a route that proceeded via 5-O-pr
Amino acids, XV: Synthesis of enantiopure DAVA-derivatives (5-amino-4-hydroxypentanoic acids) from (S)-glutamic acid
Herdeis,Lutsch,Waibel
, p. 41 - 47 (2007/10/02)
Starting from (S)-glutamic acid the readily available hydroxymethyl lactone 1 is protected as the TBDPS ether 2. Alkylation of the lithium enolate of 2 provides the lactones 3a,b with high diastereomeric excess. On the other hand 1,4 addition of Gilman cuprates to 10 furnishes the alcohols 12a,b after deprotection. Transformation of 4,12 via the mesylates 5,13 and the azides 6,14 affords the Boc protected amines 7,15 after catalytic hydrogenation in the presence of Boc2O. After treatment of 7,15 with methanolic HCl the rings of the crystalline hydrochlorides 8,16 are opened to the DAVA-derivatives (δ-aminovaleric acid derivatives) 9,17.
Regio-, stereo-, and enantioselective synthesis of cyclobutanols by means of the photoaddition of 1,3-dioxin-4-ones and lipase-catalyzed acetylation
Sato,Ohuchi,Abe,Kaneko
, p. 313 - 328 (2007/10/02)
Homochiral cis-2-hydroxymethylcyclobutanols, their all cis 3-methyl, and 4-hydroxymethyl derivatives were synthesized from 1,3-dioxin-4-ones via cyclobutane ring formation by [2+2]photocycloaddition, dioxanone ring cleavage, and reduction, followed by lip
On the stereochemical divergence in the conjugate addition of lithium dimethylcuprate/trimethylsilyl chloride to γ-alkoxy and γ-ureido α,β-unsaturated esters
Hanessian,Sumi
, p. 1083 - 1089 (2007/10/02)
A comparative study was made of the reaction of chiral nonracemic γ-alkoxy and γ-ureido-α,β-unsaturated esters with lithium dimethylcuprate in the presence of trimethylsilyl chloride. The possible origins of the anti- and syn-additions respectively are di
Synthesis and evaluation of a series of 1-(3-alkyl-2,3-dideoxy-alpha,beta-D-erythro-pentofuranosyl)thymines.
Agyei-Aye,Baker
, p. 261 - 275 (2007/10/02)
A series of 1-(3-alkyl-2,3-dideoxy-alpha,beta-D-erythro-pentofuranosyl)thymines (3'-alkyl-3'-deoxythymidines) has been prepared from 5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-D-glycero-pent-2- enono-1,4-lactone ((S)-5-[(tert-butyldiphenylsilyl)oxymethyl]-2(5H)- furanone) by Michael addition of the appropriate organocopper reagent, followed by reduction of the lactone, acetylation of the resulting hemiacetal, and trimethylsilyl triflate-catalyzed coupling with 2,4-di-O-(trimethylsilyl)thymine. The protected nucleosides were desilylated by using tetrabutylammonium fluoride to give anomeric mixtures of the free nucleosides. The unsubstituted 2',3'-dideoxynucleoside analog was similarly prepared from 5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-D-glycero-pentono- 1,4-lactone ((S)5-[(tert-butyldiphenylsilyl)-oxymethyl]-dihydro-2(3H)-fu r anone).
