256920-79-3

Upstream product

• 398518-61-1 tert-butyl-((1S,2R)-3-iodo-1-{(R)-1-[(4S,5S)-2-(4-methoxyphenyl)-5-methyl-[1,3]dioxin-4-yl]-ethyl}-2-methylpropoxy)dimethylsilane 

Downstream Products

• 256920-80-6 (Z)-(2R,3R,4R,5R,6S,10S,11R,12S)-5,11-bis(tert-butyldimethylsilanyloxy)-3,13-bis(4-methoxybenzyloxy)-2,4,6,8,10,12-hexamethyltridec-8-enal 
• 528559-58-2 (5R,6S,7Z,10S,11R)-11-[(1R,2S,3S)-2-[(4-methoxyphenyl)methoxy]-1,3-dimethyl-4-(phenylmethoxy)butyl]-5-[(1S)-2-[(4-methoxyphenyl)methoxy]-1-methylethyl]-2,2,3,3,6,8,10,13,13,14,14-undecamethyl-4,12-dioxa-3,13-disilapentadec-7-ene 
• 706815-63-6 (3Z,11Z,16Z)-(5S,6S,7R,8R,9S,13S,14S,15S)-8,14-Bis-(tert-butyl-dimethyl-silanyloxy)-5,7,9,11,13,15-hexamethyl-19-(4-phenoxy-phenyl)-nonadeca-1,3,11,16-tetraen-6-ol 
• 706815-60-3 (3Z,11Z,16Z)-(5S,6S,7R,8R,9S,13S,14S,15S)-8,14-Bis-(tert-butyl-dimethyl-silanyloxy)-19-(3-fluoro-4-methyl-phenyl)-5,7,9,11,13,15-hexamethyl-nonadeca-1,3,11,16-tetraen-6-ol 
• 706815-64-7 3-[(3Z,8Z,16Z)-(5S,6S,7S,11S,12R,13R,14S,15S)-6,12-Bis-(tert-butyl-dimethyl-silanyloxy)-14-hydroxy-5,7,9,11,13,15-hexamethyl-nonadeca-3,8,16,18-tetraenyl]-2-methyl-phenol 
• 706815-65-8 5-[(3Z,8Z,16Z)-(5S,6S,7S,11S,12R,13R,14S,15S)-6,12-Bis-(tert-butyl-dimethyl-silanyloxy)-14-hydroxy-5,7,9,11,13,15-hexamethyl-nonadeca-3,8,16,18-tetraenyl]-2-methyl-phenol 
• 706815-59-0 (3Z,11Z,16Z)-(5S,6S,7R,8R,9S,13S,14S,15S)-8,14-Bis-(tert-butyl-dimethyl-silanyloxy)-19-(3,5-difluoro-phenyl)-5,7,9,11,13,15-hexamethyl-nonadeca-1,3,11,16-tetraen-6-ol 
• 706815-57-8 (3Z,11Z,16Z)-(5S,6S,7R,8R,9S,13S,14S,15S)-8,14-Bis-(tert-butyl-dimethyl-silanyloxy)-19-(3-chloro-phenyl)-5,7,9,11,13,15-hexamethyl-nonadeca-1,3,11,16-tetraen-6-ol 
• 706815-56-7 (3Z,11Z,16Z)-(5S,6S,7R,8R,9S,13S,14S,15S)-8,14-Bis-(tert-butyl-dimethyl-silanyloxy)-19-(3-fluoro-phenyl)-5,7,9,11,13,15-hexamethyl-nonadeca-1,3,11,16-tetraen-6-ol 
• 706815-58-9 (3Z,11Z,16Z)-(5S,6S,7R,8R,9S,13S,14S,15S)-8,14-Bis-(tert-butyl-dimethyl-silanyloxy)-19-(3-methoxy-phenyl)-5,7,9,11,13,15-hexamethyl-nonadeca-1,3,11,16-tetraen-6-ol 

Relevant academic research and scientific papers

Large-Scale Synthesis of the Anti-Cancer Marine Natural Product (+)-Discodermolide. Part 4: Preparation of Fragment C7-24

Coupling of C9-14 (4) and C15-21 (5a) fragments to produce the cis-trisubstituted olefin was achieved using Suzuki-type coupling conditions employed by Marshall (5a/tert-BuLi/B-OMe-9-BBN added to 4/Cs 2CO3/Pd(dppf)2). The terminal (Z)-diene moiety was attached to aldehyde 10 by using a sequential Nozaki-Hiyama allylation and Peterson olefination sequence; careful monitoring of the disappearance of both diastereomeric β-hydroxysilanes was found to be essential for achieving a high yield. In the oxidation of alcohols 12 and 16 to 13 and 7, respectively, using iodobenzene diacetate and TEMPO, addition of a trace of water was found to be crucial for complete conversion. The C8-9 (Z)-olefin functionality was introduced on to aldehyde 13 using a Still-Gennari HWE reaction. Subsequent carbamate installation at C-19 followed by a reduction/oxidation sequence gave the title fragment C7-24 (7) ready to be coupled with the C1-6 fragment, which is described in Part 2 of this series.

Design, synthesis and cytotoxicity of 7-deoxy aryl discodermolide analogues

A series of 7-deoxy discodermolide analogues in which the lactone fragment 'C' was replaced by aryl substituents were designed, synthesized, and evaluated for cytotoxicity.