1257329-34-2

Upstream product

• 1257329-32-0 (5R,6S,8S,11R,12R,13S,14S)-11-(tert-butyldimethylsilyloxy)-5-[(S)-4-iodobut-3-yn-2-yl]-13-[(4-methoxybenzyl)oxy]-2,2,3,3,6,8,12,14,17,17,18,18-dodecamethyl-4,16-dioxa-3,17-disilanonadecane 
• 169105-67-3 (2R,4S)-5-(benzyloxy)-2,4-dimethylpentan-1-ol 
• 143236-77-5 [2S,4R]-5-(4-methoxy-benzyloxy)-2,4-dimethyl-pentan-1-ol 
• 1257329-16-0 (2R,6R,8S)-9-(benzyloxy)-2-[(4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-6,8-dimethylnon-4-yn-3-one 
• 960012-22-0 (3S,4R,5S,7S,10R,11R,12S,13S)-10,14-bis(tert-butyldimethylsilanyloxy)-12-(4-methoxybenzyloxy)-3,5,7,11,13-pentamethyltetradec-1-yn-4-ol 
• 960012-26-4 (2S,4S,7R,8R,9S,10S)-7,11-bis(tert-butyldimethylsilanyloxy)-9-(4-methoxybenzyloxy)-2,4,8,10-tetramethylundecanal 
• 960012-15-1 ({[(2S,4R)-2,4-dimethylhex-5-yn-1-yl]oxy}methyl)benzene 
• 922523-34-0 (2S,4R)-5-(4-methoxybenzyloxy)-2,4-dimethylpentanoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenylethyl)-methyl-amide 

Downstream Products

• 1257329-36-4 (2S,3S,4R,5R,8S,10S,11R,12S,Z)-5,11-bis(tert-butyldimethylsilyloxy)-14-iodo-3-(4-methoxybenzyloxy)-2,4,8,10,12-pentamethyltetradec-13-en-1-ol 
• 919298-84-3 (5R,6S,8S,11R)-5-((S,Z)-4-iodobut-3-en-2-yl)-11-((2R,3S,4S,Z)-3-(4-methoxybenzyloxy)-4-methylocta-5,7-dien-2-yl)-2,2,3,3,6,8,13,13,14,14-decamethyl-4,12-dioxa-3,13-disilapentadecane 
• 1257329-38-6 (2R,3R,4R,5R,8S,10S,11R,12S,Z)-5,11-bis(tert-butyldimethylsilyloxy)-14-iodo-3-(4-methoxybenzyloxy)-2,4,8,10,12-pentamethyltetradec-13-en-1-al 
• 1257329-44-4 (2Z,4E,6R,7S,9R,10Z,12S,13R,14S,16S,19R,20R,21S,22S,23Z)-methyl 7,13,19-tris(tert-butyldimethylsilyloxy)-9-hydroxy-21-(4-methoxybenzyloxy)-6,12,14,16,20,22-hexamethylhexacosa-2,4,10,23,25-pentaenoate 
• 1257329-46-6 (2Z,4E,6R,7S,9R,10Z,12S,13R,14S,16S,19R,20R,21S,22S,23Z)-methyl 7,9,13,19-tetrakis(tert-butyldimethylsilyloxy)-21-(4-methoxybenzyloxy)-6,12,14,16,20,22-hexamethylhexacosa-2,4,10,23,25-pentaenoate 
• 1257329-51-3 C₆₃H₁₁₁Cl₃O₈Si₄ 

Relevant academic research and scientific papers

Highly stereoselective total synthesis of (+)-9-epi-Dictyostatin and (-)-12,13-Bis-epi-dictyostatin

The total syntheses of (+)-9-epi-dictyostatin (1a) and (-)-12,13-bis-epi- dictyostatin (1b), diastereomers of the antimitotic marine sponge-derived macrolide (-)-dictyostatin (1), were achieved by creating 11 stereogenic centers and 4stereogenic double bonds with a high level of stereocontrol. The yield for the 29-step longest linear sequence from Roche ester was 1.53 and 1.52%, respectively. The final key steps to these unnatural products were the addition of vinylzincates C10-C26 to aldehyde C1-C9 (leading surprisingly to complete stereoselectivity for the 9R-configuration in 28a and for the 9S-configuration in 12,13-bis-epimeric 28b), followed by Yamaguchi macrolactonization and global deprotection. (-)-12,13-Bis-epi-dictyostatin (1b) displayed a dramatic decrease of cytotoxicity and of the affinity toward the paclitaxel binding site of microtubules. Eleven stereogenic centers and fourstereogenic double bonds were obtained with a high level of stereocontrol in the total synthesis of (+)-9-epi-dictyostatin and(-)-12,13-bis-epi-dictyostatin, diastereomers of the antimitotic marine sponge-derived macrolide (-)-dictyostatin.

A highly stereoselective total synthesis of (+)-9-epi-dictyostatin

The total synthesis of (+)-9-epi-dictyostatin (1b), a diastereomer of the antimitotic marine-sponge-derived macrolide (-)-dictyostatin (1a), was achieved by creating 11 stereogenic centers and 4 stereogenic double bonds with a high level of stereocontrol.