213402-48-3

Upstream product

• 213402-26-7 (4R,5R)-2-(4-Methoxy-phenyl)-5-methyl-[1,3]dioxane-4-carbaldehyde 
• 213402-37-0 1-[(4R,5R)-2-(4-Methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-propan-1-one 
• 213402-21-2 [(4R,5R)-2-(4-Methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-methanol 
• 213402-32-5 1-[(4R,5R)-2-(4-Methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-propan-1-ol 
• 213402-41-6 (4R,5R)-2-(4-Methoxy-phenyl)-5-methyl-4-(1-methylene-propyl)-[1,3]dioxane 
• 2186-92-7 p-Anisaldehyde dimethyl acetal 

Downstream Products

• 213402-55-2 (R)-2-[(4R,5R)-2-(4-Methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-butyraldehyde 
• 213402-69-8 (2R,3S,4S)-4-[(4R,5R)-2-(4-Methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2-methyl-hexane-1,3-diol 
• 213402-89-2 tert-Butyl-((1S,2R)-1-{(R)-1-[(4R,5R)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-propyl}-2-methyl-pent-4-ynyloxy)-dimethyl-silane 
• 213402-62-1 (S)-4-Benzyl-3-{(2S,3R,4S)-3-hydroxy-4-[(4R,5R)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2-methyl-hexanoyl}-oxazolidin-2-one 
• 213408-85-6 (3Z,5E,13E,15E)-(7R,8R,9S,10S,11R,17S,18R)-8,10-Bis-(diethyl-isopropyl-silanyloxy)-9-ethyl-3,17-dimethoxy-18-{(S)-2-[(4-methoxy-phenyl)-diphenyl-methoxy]-1-methyl-ethyl}-5,7,11,13-tetramethyl-oxacyclooctadeca-3,5,13,15-tetraen-2-one 
• 213408-84-5 (2Z,4E,12E,14E)-(6R,7R,8S,9S,10R,16S,17R,18S)-7,9-Bis-(diethyl-isopropyl-silanyloxy)-8-ethyl-17-hydroxy-2,16-dimethoxy-19-[(4-methoxy-phenyl)-diphenyl-methoxy]-4,6,10,12,18-pentamethyl-nonadeca-2,4,12,14-tetraenoic acid 
• 213408-83-4 (2Z,4E,12E,14E)-(6R,7R,8S,9S,10R,16S,17R,18S)-7,9-Bis-(diethyl-isopropyl-silanyloxy)-8-ethyl-17-hydroxy-2,16-dimethoxy-19-[(4-methoxy-phenyl)-diphenyl-methoxy]-4,6,10,12,18-pentamethyl-nonadeca-2,4,12,14-tetraenoic acid methyl ester 
• 213402-76-7 Toluene-4-sulfonic acid (2R,3S,4S)-3-hydroxy-4-[(4R,5R)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2-methyl-hexyl ester 
• 213402-83-6 Toluene-4-sulfonic acid (2R,3S,4R)-3-(tert-butyl-dimethyl-silanyloxy)-4-[(4R,5R)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2-methyl-hexyl ester 

Relevant academic research and scientific papers

The first total synthesis of concanamycin F (concanolide A)

A highly stereoselective total synthesis of the macrolide antibiotic concanamycin F (1), a specific and potent inhibitor of vacuolar H+-ATPase, has been achieved by a convergent route involving the synthesis and coupling of its 18-membered tetraenic lactone and β-hydroxyl hemiacetal side chain subunits. The C1-C19 18-membered lactone aldehyde 4 was synthesized through the intermolecular Stille coupling of the C5-C13 vinyl iodide 24 and the C14-C19 vinyl stannane 25, followed by construction of the C1-C4 diene and macrolactonization. Synthesis of 4 via a second convergent route including the esterification of the C1-C13 vinyl iodide 45 and the C14-C19 vinyl stannane 47 followed by the intramolecular Stille coupling was also realized. The highly stereoselective aldol coupling of 4 and the C20-C28 ethyl ketone 5 followed by desilylation provided 1 which was identical with natural concanamycin F.

Synthetic studies on concanamycin A: Synthesis of the C5~C13 and C20~C28 segments

The enantioselective synthesis of the C5~C13 (2) and C20~C28 (3) segments, which are promising synthetic intermediates toward the total synthesis of the 18-membered macrolide antibiotic, concanamycin A (1), were described.