866138-90-1

Upstream product

• 866138-76-3 (R)-4-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)pentanoic acid 
• 86771-48-4 (4R)-4-[(4-methoxybenzyl)oxymethyl]-γ-butyrolactone 
• 77697-15-5 (R)-(-)-γ-benzyloxymethyl-γ-butyrolactone 
• 52813-63-5 (5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone 
• 866138-77-4 (R)-4-benzyl-3-((R)-4-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)pentanoyl)oxazolidin-2-one 

Downstream Products

• 866138-78-5 ethyl (2E,4R)-7-((R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl)-4-(tert-butyldimethylsilyloxy)-7-oxohept-2-enoate 
• 866138-95-6 ethyl (2E,4R,6S,7S,10S,12E)-4-(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-7-hydroxy-6-(hydroxymethyl)tetradeca-2,12-dienoate 
• 866138-97-8 ethyl (2E,4R,6S,7S,10S,12E)-4-(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-7-hydroxy-6-((2-pyridylselenyl)methyl)tetradeca-2,12-dienoate 
• 866138-98-9 (2E,12E)-(4R,6R,7S,10S)-4-(tert-Butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-7-methanesulfonyloxy-6-(pyridin-2-ylselanylmethyl)-tetradeca-2,12-dienoic acid ethyl ester 
• 866138-87-6 ethyl (2E,4R,6R,7S,10S,12E)-6-((R)-4-benzyl-2-oxo-1,3-oxazolidine-3-carbonyl)-4-(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-7-hydroxytetradeca-2,12-dienoate 
• 866138-88-7 ethyl (2E,4R,6S,7S,10S,12E)-4-(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-7-hydroxy-6-(trityloxymethyl)tetradeca-2,12-dienoate 
• 866138-96-7 ethyl (2E,4R,6S,7S,10S,12E)-4-(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-7-(methanesulfonyloxy)-6-(trityloxymethyl)tetradeca-2,12-dienoate 
• 866138-91-2 (R)-5-((R)-4-Benzyl-2-oxo-oxazolidin-3-yl)-2-(tert-butyl-dimethyl-silanyloxy)-5-oxo-pentanal 

Relevant academic research and scientific papers

Svetamycins A-G, Unusual Piperazic Acid-Containing Peptides from Streptomyces sp.

Seven new halogenated peptides termed svetamycins A-G (1-7) have been isolated from laboratory cultures of a Streptomyces sp. Svetamycins A-D, F, and G are cyclic depsipeptides, whereas svetamycin E is a linear analogue of svetamycin C. Their structures were determined using extensive spectroscopic analysis, and their stereochemical configuration was established by a combination of NMR data, quantum mechanical calculations, and chemical derivatizations. Svetamycins are characterized by the presence of a hydroxyl acetic acid and five amino acids including a rare 4,5-dihydroxy-2,3,4,5-tetrahydropyridazine-3-carboxylic acid, a γ-halogenated piperazic acid, and a novel δ-methylated piperazic acid in svetamycins B-C, E, and G. Moreover, isotope-labeled substrate feeding experiments demonstrated ornithine as the precursor of piperazic acid and that methylation at the δ position of the piperazyl scaffold is S-adenosyl-l-methionine (SAM)-dependent. Svetamycin G, the most potent antimicrobial of this suite of compounds, inhibited the growth of Mycobacterium smegmatis with an MIC80 value of 2 μg/mL.

Synthesis of (-)-amphidinolide K fragment C9-C22

(Chemical Equation Presented) The key fragment (2a or 2b) in a total synthesis of the cytotoxic macrolide (-)-amphidinolide K (1) has been achieved from synthons C9-C14 (3) and C15-C22 (4), which have both been prepared from glutamic acid in good overall yields.