1294479-62-1

Upstream product

• 1116503-88-8 ethyl (2R,3S)-3-hydroxy-2-(((4-nitrophenyl)sulfonyl)oxy)-3-phenylpropanoate 
• 1116503-90-2 (2S,3S)-ethyl 2-azido-3-hydroxy-3-phenylpropanoate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 119364-52-2 (1S,2R)-2-amino-1-phenylpropane-1,3-diol 
• 108741-14-6 (2R,3S)-ethyl 2,3-dihydroxy-3-phenylpropanoate 
• 4192-77-2 ethyl cinnamate 
• 488727-71-5 (4R)-(1-hydroxy-phenyl-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 95715-87-0 (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine 
• 108-86-1 bromobenzene 
• 1377320-83-6 (R)-4-[(S)-hydroxy(phenyl)methyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester 
• 488727-73-7 (4R)-benzoyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 

Downstream Products

• 32946-42-2 (2S,3S)-2-amino-3-hydroxy-3-phenylpropanoic acid 
• 487060-72-0 (2S,3S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-hydroxy-3-phenylpropanoic acid 

Relevant academic research and scientific papers

Synthetic Studies Toward the Skyllamycins: Total Synthesis and Generation of Simplified Analogues

Herein, we report our synthetic studies toward the skyllamycins, a highly modified class of nonribosomal peptide natural products which contain a number of interesting structural features, including the extremely rare α-OH-glycine residue. Before embarking on the synthesis of the natural products, we prepared four structurally simpler analogues. Access to both the analogues and the natural products first required the synthesis of a number of nonproteinogenic amino acids, including three β-OH amino acids that were accessed from the convenient chiral precursor Garner's aldehyde. Following the preparation of the suitably protected nonproteinogenic amino acids, the skyllamycin analogues were assembled using a solid-phase synthetic route followed by a final stage solution-phase cyclization reaction. To access the natural products (skyllamycins A-C) the synthetic route used for the analogues was modified. Specifically, linear peptide precursors containing a C-terminal amide were synthesized via solid-phase peptide synthesis. After cleavage from the resin the N-terminal serine residue was oxidatively cleaved to a glyoxyamide moiety. The target natural products, skyllamycins A-C, were successfully prepared via a final step cyclization with concomitant formation of the unusual α-OH-glycine residue. Purification and spectroscopic comparison to the authentic isolated material confirmed the identity of the synthetic natural products.

Total Synthesis of Skyllamycins A–C

The skyllamycins are a family of highly functionalized non-ribosomal cyclic depsipeptide natural products which contain the extremely rare α-OH-glycine functionality. Herein the first total synthesis of skyllamycins A–C is reported, together with the biofilm inhibitory activity of the natural products. Linear peptide precursors for each natural product were prepared through an efficient solid-phase route incorporating a number of synthetic modified amino acids. A novel macrocyclization step between a C-terminal amide and an N-terminal glyoxylamide moiety served as a key transformation to install the unique α-OH-glycine unit and generate the natural products in the final step of the synthesis.

Highly enantioselective synthesis of anti aryl β-hydroxy α-amino esters via DKR transfer hydrogenation

An efficient preparation of highly enantiomerically enriched aryl β-hydroxy α-amino esters via dynamic kinetic resolution (DKR), asymmetric transfer hydrogenation of α-amino β-keto esters is described. The anti β-hydroxyl α-amino esters were obtained both in high yields and high diasteroselectivity. The observed high anti selectivity is inconsistent with the previous results in literature. The absolute stereochemistry of the aryl β-hydroxy α-amino esters was unambiguously confirmed via chemical derivatization as well as Vibrational Circular Dichroism (VCD) techniques.