25129-91-3

Usage

Uses

Albocycline is an antibiotic with selectivity mainly against staphylococci.

InChI:InChI=1/C18H28O4/c1-13-7-6-8-14(2)16(21-5)9-11-18(4,20)12-10-17(19)22-15(13)3/h8-13,15-16,20H,6-7H2,1-5H3/b11-9+,12-10+,14-8+/t13-,15+,16-,18+/m0/s1

Upstream product

• 87518-68-1 (3E,6E,9E)-(5R,8S,13S,14R)-8-Methoxy-5,9,13,14-tetramethyl-5-(tetrahydro-pyran-2-yloxy)-oxacyclotetradeca-3,6,9-trien-2-one 
• 114972-63-3 (E)-(2R,7S,8R)-8-Benzyloxymethoxy-2-methoxy-3,7-dimethyl-non-3-en-1-ol 
• 114972-46-2 Toluene-4-sulfonic acid (2S,3S)-4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-3-methyl-butyl ester 
• 114972-53-1 (E)-(S)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-4-(tetrahydro-pyran-2-yloxy)-pent-2-enoic acid methyl ester 
• 114972-64-4 (E)-(2R,7S,8R)-8-Benzyloxymethoxy-2-methoxy-3,7-dimethyl-non-3-enal 
• 114972-50-8 1-((2R,3R)-3-Benzyloxymethoxy-2-methyl-butane-1-sulfonyl)-4-methyl-benzene 
• 497-03-0 2-methylbut-2-enal 
• 1428737-96-5 C₁₄H₂₀O₄ 
• 66767-61-1 methyl 2R,3R-nilate 
• 1164192-58-8 (2E,5E,8E)-(4R,7S,12S,13R)-13-Benzyloxymethoxy-7-methoxy-4,8,12-trimethyl-4-(tetrahydro-pyran-2-yloxy)-tetradeca-2,5,8-trienoic acid methyl ester 
• 114972-67-7 (2E,5E,8E)-(4R,7S,12S,13R)-13-Benzyloxymethoxy-7-methoxy-4,8,12-trimethyl-4-(tetrahydro-pyran-2-yloxy)-tetradeca-2,5,8-trienoic acid 
• 114972-57-5 (E)-(S)-4-Methyl-4-(tetrahydro-pyran-2-yloxy)-5-trifluoromethanesulfonyloxy-pent-2-enoic acid methyl ester 

Relevant academic research and scientific papers

Total Synthesis of (?)-Albocycline

The macrolactone natural product (?)-albocycline is a promising antibiotic candidate for the treatment of both methicillin resistant Staphylococcus aureus (MRSA) and vancomycin-resistant strains. Herein we report a concise total synthesis of (?)-albocycline in 14 steps from commercially available methyl (R)-3-hydroxybutyrate. Novel key steps include the highly regio- and stereoselective reactions of chiral N-sulfinyl metallodienamines (NSMDs) with aldehydes and the Davis oxaziridine, in addition to the Horner–Wadsworth–Emmons olefination of N-sulfinyl imines.

Enantioselective total synthesis of ingramycin

An enantioselective total synthesis of the 14-membered macrolide antibiotic ingramycin, 1, is described. In a convergent approach three chiral fragments A,B and C are assembled, the allylic bromide A deriving its chirality from L-serine while the asymmetr

Tin-mediated esterification in macrolide synthesis

A neutral and relatively simple new method for effecting internal macrocyclic esterification of omega -hydroxycarboxylic acids, based on a tin 'template-driven' extrusion process, is discussed and its application to the synthesis (macrocyclization step) of the macrolide antibiotics zearalenone, ingramycin, and nodusmicin detailed. An efficient, formal total synthesis of pyrenophorin using this technique is also presented. Attempts to extend the methodology to include the macrocyclization of omega -bromo carboxylic acids or omega -mercapto carboxylic acids were unsuccessful. However, although beta - and omega -amino carboxylic acids preferentially gave way to polymer formation, 4-,5, and 6-amino carboxylic acids readily condensed to give the corresponding five-, six-, and seven-membered lactams in excellent yields. For example, in this way, the bridged lactam 1-azabicyclo- left bracket 3. 3. 1 right bracket nonan-2-one was prepared in 77% yield as compared to the previously reported yield of less than 2%.