213408-83-4

Upstream product

• 14470-28-1 mono-4-methoxytrityl chloride 
• 213408-82-3 (2Z,4E,12E,14E)-(6R,7R,8S,9S,10R,16S,17R,18S)-7,9-Bis-(diethyl-isopropyl-silanyloxy)-8-ethyl-17,19-dihydroxy-2,16-dimethoxy-4,6,10,12,18-pentamethyl-nonadeca-2,4,12,14-tetraenoic acid methyl 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 
• 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 
• 213408-81-2 (2Z,4E,12E,14E)-(6R,7R,8S,9S,10R,16S)-7,9-Bis-(diethyl-isopropyl-silanyloxy)-8-ethyl-2,16-dimethoxy-4,6,10,12-tetramethyl-16-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-hexadeca-2,4,12,14-tetraenoic acid methyl ester 
• 213408-78-7 (2E,10E,12E)-(4R,5R,6S,7S,8R,14S)-5,7-Bis-(diethyl-isopropyl-silanyloxy)-6-ethyl-14-methoxy-2,4,8,10-tetramethyl-14-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-tetradeca-2,10,12-trienoic acid ethyl ester 
• 213408-75-4 2,2-Dimethyl-propionic acid (8E,10E)-(2R,3R,4S,5S,6R,12S)-3,5-bis-(diethyl-isopropyl-silanyloxy)-4-ethyl-12-methoxy-2,6,8-trimethyl-12-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-dodeca-8,10-dienyl ester 
• 213408-79-8 (2E,10E,12E)-(4R,5R,6S,7S,8R,14S)-5,7-Bis-(diethyl-isopropyl-silanyloxy)-6-ethyl-14-methoxy-2,4,8,10-tetramethyl-14-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-tetradeca-2,10,12-trien-1-ol 
• 213408-80-1 (2E,10E,12E)-(4R,5R,6S,7S,8R,14S)-5,7-Bis-(diethyl-isopropyl-silanyloxy)-6-ethyl-14-methoxy-2,4,8,10-tetramethyl-14-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-tetradeca-2,10,12-trienal 
• 213408-77-6 (8E,10E)-(2S,3S,4S,5S,6R,12S)-3,5-Bis-(diethyl-isopropyl-silanyloxy)-4-ethyl-12-methoxy-2,6,8-trimethyl-12-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-dodeca-8,10-dienal 
• 213408-76-5 (8E,10E)-(2R,3R,4S,5S,6R,12S)-3,5-Bis-(diethyl-isopropyl-silanyloxy)-4-ethyl-12-methoxy-2,6,8-trimethyl-12-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-dodeca-8,10-dien-1-ol 
• 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 
• 213402-11-0 2,2-Dimethyl-propionic acid (E)-(2R,3R,4S,5S,6R)-3,5-bis-(diethyl-isopropyl-silanyloxy)-4-ethyl-9-iodo-2,6,8-trimethyl-non-8-enyl ester 
• 213403-07-7 2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-3,5-bis-(diethyl-isopropyl-silanyloxy)-4-ethyl-2,6-dimethyl-non-8-ynyl ester 

Downstream Products

• 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 
• 213408-85-6 (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 

Relevant academic research and scientific papers

Synthetic studies on concanamycin A: Total synthesis of concanolide A (concanamycin F)

Enantioselective first total synthesis of concanolide A (concanamycin F), which is one of a new class of macrolide antibiotics, concanamycins, has been achieved by a highly effective and convergent route.

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.