304671-65-6

Upstream product

• 252342-41-9 (R)-4-Benzyl-3-{(2R,3S,4S)-3-hydroxy-4-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2-methyl-pentanoyl}-oxazolidin-2-one 
• 132969-62-1 (2'R,3'S,4'S,4R,5S)-3-[3'-hydroxy-5'-(4-methoxyphenyl)methoxy-2',4'-dimethylpentanoyl]-5-phenyl-4-methyl-2-oxazolidinone 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 303727-86-8 (R)-4-Benzyl-3-{(2R,3S,4R)-3-(tert-butyl-dimethyl-silanyloxy)-4-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2-methyl-pentanoyl}-oxazolidin-2-one 
• 303727-84-6 (R)-N-methoxy-2-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxinan-4-yl]-N-methylpropionamide 
• 303727-85-7 (R)-2-[(4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxinan-4-yl]propionaldehyde 

Downstream Products

• 252342-52-2 (Z)-(2S,3R,4S,8S,9R,10R)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-10-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2,4,6,8-tetramethyl-undec-5-en-1-ol 
• 252342-46-4 (5Z,13Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-hexadeca-5,13,15-trien-1-ol 
• 252342-44-2 (2S,4S,5S)-4-[(Z)-(1R,2R,3S,7S,8R,9S)-2,8-bis(tert-butyldimethylsilanyloxy)-10-(4-methoxybenzyloxy)-1,3,5,7,9-pentamethyldec-5-enyl]-2-(4-methoxyphenyl)-5-methyl-[1,3]dioxane 
• 342905-45-7 (Z)-(2R,3R,4R,5R,6S,10S,11R,12S)-5,11-Bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-13-trityloxy-tridec-8-enal 
• 252342-45-3 (2S,4S,5S)-4-[(Z)-(1R,2R,3S,7S,8R,9S)-2,8-Bis-(tert-butyl-dimethyl-silanyloxy)-1,3,5,7,9-pentamethyl-10-trityloxy-dec-5-enyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane 
• 252342-53-3 (Z)-(2S,3S,4R,5R,6S,10S,11R,12S)-5,11-Bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-13-trityloxy-tridec-8-en-1-ol 
• 303728-22-5 1-[(Z)-(1S,2R,3R,4S,8S,9R,10S)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-2,4,6,8,10-pentamethyl-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-11-trityloxy-undec-6-enyloxymethyl]-4-methoxy-benzene 
• 252342-47-5 4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-[2,6,12-tris-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-5,7,9,11,13,15-hexamethyl-nonadeca-3,8,16,18-tetraenyl]-tetrahydro-pyran-2-one 

Relevant academic research and scientific papers

Evolution of a gram-scale synthesis of (+)-discodermolide

An efficient, highly convergent, stereocontrolled total synthesis of the potent antimitotic agent (+)-discodermolide (1) has been achieved on gram scale. Key elements of the successful strategy include (1) elaboration of three advanced fragments from a common precursor (CP) which embodies the repeating stereochemical triad of the discodermolide backbone, (2) σr-bond installation of the Z trisubstituted olefin, exploiting a modified Negishi cross-coupling reaction, (3) synthesis of a late-stage phosphonium salt utilizing high pressure, and (4) Wittig installation of the Z disubstituted olefin and the terminal (Z)-diene.

Gram-scale synthesis of (+)-discodermolide.

[formula: see text] A triply convergent, highly efficient second-generation synthesis of the potent antimitotic agent (+)-discodermolide (1) has been achieved on a 1-g scale.