136266-35-8

Usage

InChI:InChI=1/C18H30O8/c1-2-3-4-5-6-7-8-9-10-11-12-24-18(22)15-13(16(20)26-23)14(19)17(21)25-15/h13-15,19,23H,2-12H2,1H3/t13-,14-,15+/m1/s1

Upstream product

• 193957-74-3 benzyl-(3R,4S,5S)-2-oxo-3,4-dihydroxy-4-carboxy-5-dodecyl-tetrahydrofuran-5-carboxylate 
• 1194525-28-4 methyl rac-(E,R)-2-(phenylselenyl)-3,4-bis(methoxycarbonyl)-3-hexadecenoate 
• 1194525-26-2 methyl rac-(2Z,4R)-4-hydroxy-3,4-bis(methoxycarbonyl)-2-hexadecenoate 
• 1194525-25-1 methyl rac-(R)-3-hydroxy-3-(methoxycarbonyl)-2-oxopentadecanoate 
• 1194525-23-9 methyl 2-(tert-butyldimethylsilyloxy)-3-(methoxycarbonyl)-2-pentadecenoate 
• 1194525-27-3 methyl rac-(R)-3-(phenylselenyl)-3-(methoxycarbonyl)-2-oxopentadecanoate 
• 124-10-7 methyl myristoate 
• 1429481-07-1 7-(benzyloxy)-6-((benzyloxy)methyl)-2,2-dimethyldihydro-4H-4a,7a-(methanooxymethano)furo[3,2-d]-[1,3]dioxin-10-one 
• 1429481-05-9 (2R,3R,3aS,6aS)-3-(benzyloxy)-2-((benzyloxy)methyl)-tetrahydro-3a-hydroxy-6a-(hydroxymethyl)furo[3,4-b]furan-6-(6aH)-one 
• 1429481-16-2 tert-butyl (4aS,7S,7aS)-7-(benzyloxy)-4a-dodecyltetrahydro-2,2-dimethyl-6-oxo-4H-furo[3,2-d][1,3]dioxine-7a-carboxylate 
• 1429481-15-1 C₃₃H₅₂O₈ 

Relevant academic research and scientific papers

Enantiospecific synthesis of the phospholipase A2 inhibitors (-)-cinatrin C1 and (+)-cinatrin C3

The enantiospecific synthesis of (-)-cinatrin C1 (3) and (-)-cinatrin C3 (5) from the D-arabinose derivative 9 is described. The stereochemistry at C2 was introduced via a chelation-controlled addition of a carbanion to a-hydroxy ketone 8. The best selectivity was achieved by use of the Grignard reagent derived from trimethylsilylacetylene. Transformation of the terminal alkyne into methyl ester 17 followed by acetal hydrolysis and selective lactol oxidation gave cinatrin C1 dimethyl ester (7). Base hydrolysis and acid induced relactonization then gave a 1 : 1 mixture of cinatrins C1 (3) and C3 (5).

Total synthesis of (-)-cinatrin C1 based on an In(OTf) 3-catalyzed Conia-ene reaction

The stereocontrolled total synthesis of (-)-cinatrin C1, a phospholipase A2 inhibitor, has been accomplished. The key feature includes the stereoselective construction of the highly substituted tetrahydrofuran core by In(OTf)3-catalyzed Conia-ene reaction of the oxygen-tethered acetylenic malonic ester followed by dihydroxylation with concomitant lactonization.

METHOD FOR OBTAINING CINATRINS C3 AND C1

The present invention relates to a process for obtaining cinatrins C1 and C3 and derivatives thereof which comprises the hydroxylation of a compound of formula (III). The invention also relates to the intermediates of said synthesis

Aldol reactions of ketal-protected tartrate ester enolates. Asymmetric syntheses and absolute stereochemical assignments of phospholipase A2 inhibitors cinatrin C1 and C3

An efficient approach to the syntheses of cinatrins C1 and C3 has been developed and used to establish the absolute configurations of these natural products. The construction of each molecule has been achieved in a five-step reaction sequence (overall yield 43% for cinatrin C1, 33% for cinatrin C3) from the di-tert-butyl ester of (R,R)-tartaric acid. The two contiguous, quaternary chiral centers in the cinatrin skeleton are constructed via a diastereoselective, titanium-mediated aldol coupling of a tartrate-derived silylketene acetal and an achiral α-ketoester. This bond construction proceeds with excellent diastereoselectivity for a variety of aldehyde and α-ketoester substrates.