157020-34-3

Upstream product

• 161458-78-2 (2R,4R)-4-(hydroxymethyl)-2-phenylthiazolidine-3-carboxylic acid tert-butyl ester 
• 1027267-16-8 (2R,4R)-2-Phenyl-thiazolidine-3,4-dicarboxylic acid 3-tert-butyl ester 4-methyl ester 
• 196930-46-8 (4R)-2-phenyl-1,3-thiazolidine-4-carboxylic acid 
• 100-52-7 benzaldehyde 
• 64970-78-1 (2R,4R)-2-phenyl-1,3-thiazolidine-4-carboxylic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 158446-52-7 (2R,4R)-3-(tert-butoxycarbonyl)-2-phenylthiazolidine-4-carboxylic acid 
• 189228-43-1 (2RS,4R)-2-phenylthiazolidine-4-carboxylic acid ethyl ester 
• 99380-83-3 (2RS,4R)-4-(hydroxymethyl)-2-phenylthiazolidine 

Downstream Products

• 157020-35-4 cis-4(R)-(6-Carboxyhex-1-enyl)-2(R)-phenylthiazolidine-3-carboxylic acid tert-butyl ester 
• 185146-31-0 (2R,4R)-4-((1Z,5E,7E)-(R)-11-Methoxy-8-methyl-tetradeca-1,5,7,13-tetraenyl)-2-phenyl-thiazolidine-3-carboxylic acid tert-butyl ester 
• 449729-37-7 (2R,4R)-4-((S)-Cyano-trimethylsilanyloxy-methyl)-2-phenyl-thiazolidine-3-carboxylic acid tert-butyl ester 
• 452100-77-5 (2R,4R)-4-(Cyano-trimethylsilanyloxy-methyl)-2-phenyl-thiazolidine-3-carboxylic acid tert-butyl ester 
• 449729-42-4 (S)-7-[(2R,4R)-3-(tert-butoxycarbonyl)-2-phenylthiazolidin-4-yl]-7-hydroxy-6-oxoheptanoic acid methyl ester 
• 449729-39-9 (S)-7-[(2R,4R)-3-(tert-butoxycarbonyl)-2-phenylthiazolidin-4-yl]-7-hydroxy-6-oxoheptanoic acid 
• 449729-44-6 (S)-7-[(2R,4R)-3-(tert-butoxycarbonyl)-2-phenylthiazolidin-4-yl]-7-methoxycarbonyloxy-6-oxoheptanoic acid methyl ester 
• 161458-90-8 (2R,4R)-4-((Z)-6-Methoxycarbonyl-hex-1-enyl)-2-phenyl-thiazolidine-3-carboxylic acid tert-butyl ester 
• 1026489-89-3 (Z)-(R)-9-Benzylsulfanyl-8-tert-butoxycarbonylamino-non-6-enoic acid methyl ester 
• 1068134-56-4 (2R,4R)-2-phenyl-4-vinylthiazolidine-3-tert-butyl carboxylate 

Relevant academic research and scientific papers

Stereospecific total synthesis of somocystinamide A

(Chemical Equation Presented) The first total synthesis of somocystinamide A, a disulfide dimer with extremely labile enamide functional groups, was accomplished in a concise and stereospecific manner. Somocystinamide A is reported to possess exceptionall

A novel synthesis of (+)-biotin from L-cysteine

(+)-Biotin (1) was synthesized in 25% overall yield over 11 steps from L-cysteine. The contiguous asymmetric centers at C-3a and C-6a were formed through a novel and highly stereoselective Lewis base-catalyzed cyanosilylation of α-amino aldehyde 3 to provide anti- O-TMS-cyanohydrin 4 with high stereoselectivity and in high yield (anti/syn = 92:8, 96%). Treatment of 4 with a di-Grignard reagent, 1,4-bis(bromomagnesio)butane, followed by carbon dioxide, efficiently installed the 4-carboxybutyl chain at C-4 to give keto acid 5. The final cyclization to bicyclic compound 7b, a precursor to 1, was realized by a palladium-catalyzed intramolecular allylic amination of cis-allylic carbonate 6b that was elaborated from 5.

Absolute configuration and total synthesis of (+)-curacin A, an antiproliferative agent from the cyanobacterium Lyngbya majuscula

The absolute configuration of curacin A was determined as (2R,13R,19R,21S)-1 by comparison of degradation products 2 and 3 with the same materials prepared by asymmetric synthesis. The total synthesis of 1 was completed from (1R,2S)-2-methylcyclopropaneca

Novel Enantioselective Syntheses of (+)-Biotin

Two conceptually attractive enantioselective syntheses of (+)-biotin from L-cysteine are reported based upon an intramolecular 1,3-dipolar cycloaddition of a carbamoyl azide.The first approach (12 steps) involves the following as key-steps: (i) the macrothiolactonization of acid 10b to Z-olefin 14, (ii) the thermolysis of the ene carbamoyl azide 15 in water with direct formation of a mixture of the benzylated derivatives of (+)-biotin 16a and 17a.The second approach (14 steps) involves the following: (i) elimination of bromide 29 to the endocyclic thioenol ether 30, (ii) thermolysis of the ene carbamoyl azide 30 to the exocyclic thioenol ethers 31a and 31b.Both the synthesis of 29 and the final transformation of 31a and 31b into (+)-biotin are based upon literature precedents.