127791-71-3

Upstream product

• 127762-65-6 methyl 4-benzyloxy-c-6-(1'-hydroxyallyl)-c-9-methyl-2-oxo-(r-5-)-1-oxaspiro<4.5>dec-3-ene-t-8-carboxylate 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 127762-65-6 methyl 4-benzyloxy-c-6-(1'-hydroxyallyl)-c-9-methyl-2-oxo-(r-5-)-1-oxaspiro<4.5>dec-3-ene-c-8-carboxylate 
• 100-51-6 benzyl alcohol 
• 127853-42-3 (1S,2R,5S)-5-[1,3]Dioxolan-2-yl-2-methyl-4-oxo-cyclohexanecarboxylic acid methyl ester 
• 127853-58-1 methyl 4-(ethylthio)-c-6-formyl-c-9-methyl-2-oxo-(r-5-)-1-oxaspiro<4.5>dec-3-ene-t-8-carboxylate 
• 127762-57-6 methyl 4-benzyloxy-c-6-(1,3-dioxolan-2-yl)-c-9-methyl-2-oxo-(r-5-)-1-oxaspiro<4.5>dec-3-ene-c-8-carboxylate 
• 127762-63-4 methyl 4-benzyloxy-c-6-formyl-c-9-methyl-2-oxo-(r-5-)-1-oxaspiro<4.5>dec-3-ene-c-8-carboxylate 
• 127853-49-0 methyl c-6-(1,3-dioxolan-2-yl)-4-(ethylthio)-c-9-methyl-2-oxo-(r-5-)-1-oxaspiro<4.5>dec-3-ene-c-8-carboxylate 
• 127762-56-5 methyl c-6-(1,3-dioxolan-2-yl)-4-(ethylsulfinyl)-c-9-methyl-2-oxo-(r-5)-1-oxaspiro<4.5>dec-3-ene-c-8-carboxylate 
• 127762-21-4 methyl (E)-β-benzyloxyacrylate 
• 127762-22-5 (E)-3-(benzyloxy)acrylic acid 
• 127853-50-3 methyl c-6-(1,3-dioxolan-2-yl)-4-(ethylthio)-c-9-methyl-2-oxo-(r-5-)-1-oxaspiro<4.5>dec-3-ene-t-8-carboxylate 

Downstream Products

• 127762-68-9 methyl 4-benzyloxy-c-<1'-(tert-butyldimethylsilyloxy)allyl>-c-9-methyl-2-oxo-3-pivaloyloxy-(r-5)-1-oxaspiro<4.5>dec-3-ene-c-8-carboxylate 
• 127762-66-7 4-benzyloxy-c-6-<1'-(tert-butyldimethylsilyloxy)allyl>-c-9-methyl-2-oxo-(r-5-)-1-oxaspiro<4.5>dec-3-ene-c-8-carboxylic acid 
• 127762-66-7 4-benzyloxy-c-6-<1'-(tert-butyldimethylsilyloxy)allyl>-c-9-methyl-2-oxo-(r-5-)-1-oxaspiro<4.5>dec-3-ene-t-8-carboxylic acid 

Relevant academic research and scientific papers

Functionally Substituted Vinyl Carbanions, 42: Synthesis of the Top Half of Chlorothricolide

β-Lithiated functionally substituted acrylates 2a-c prove to be versatile building blocks for spirotetronate syntheses useful in top half syntheses of the aglycon chlorothricolide 1 of the macrolide antibiotic chlorothricin.The electrophilic-nucleophilic cyclohexanone derivatives 27-cis/trans (with relative cis or trans relationship of the carboxylate group) required in this synthesis design are obtained via a cycloaddition route from pentenone in five steps.Generation of the dilithiated species from the acrylates 2a-c affords then the corresponding spirotetronates 32a-c, which serve as versatile intermediates in top half syntheses for different strategies in chlorothricolide total syntheses.Hydroxylation in the vinylic α-position of the tetronate moiety and selective phenylselenylation provide the spirotetronates 39a-cis/trans and 41a, which meet the requirements of a top half molecule.The same is true for a different strategy, which provides the aldehydes 42b-cis/trans.The latter are then converted into the fully functionalized spirotetronates 44b-cis/trans by treatment with vinylmagnesium bromide and subsequent hydroxylation at the vinylic α-position.The investigations delineate similar convenient strategies for the syntheses of kijanolide and tetronolide, which are the aglycon portions of the structurally related macrolide antibiotics kijanimicin and tetrocarcin, respectively.