522665-54-9

Upstream product

• 106357-33-9 (4S,5S)-2-[(2Z)-2-butenyl]-1,3,2-dioxaborolane-4,5-dicarboxylic acid bis(1-methylethyl) ester 
• 132969-60-9 (2S)-3-[(4-methoxybenzyl)oxy]-2-methylpropanal 
• 31197-41-8 crotyltributylstannane 

Downstream Products

• 1185750-50-8 C₃₂H₄₄O₅Si 
• 1185750-23-5 (3S,4R,5S)-4-(4-methoxybenzyloxy)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhex-1-ene 
• 1185750-49-5 (2R,4R,5S)-4-((S)-but-3-en-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxane 
• 1185750-26-8 (2S,3R,4S,6S)-1-(benzyloxy)-8-((2R,4R,5S,6S)-6-((S)-hexan-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-2,4,6-trimethyloctan-3-ol 
• 1185750-21-3 (2S,3R,4S,5E,7E)-1-(benzyloxy)-8-((2R,4R,5S,6S)-6-((S,Z)-hexa-3,5-dien-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-2,4,6-trimethylocta-5,7-dien-3-ol 
• 1185750-52-0 (S)-2-((2S,4S,5R,6S)-6-ethynyl-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)propan-1-ol 
• 1185750-22-4 (2S,4S,5R,6S)-4-ethynyl-6-((S,Z)-hexa-3,5-dien-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxane 
• 1185750-51-9 tert-butyl((S)-2-((2S,4S,5R,6S)-2-(4-methoxyphenyl)-5-methyl-6-((trimethylsilyl)ethynyl)-1,3-dioxan-4-yl)propoxy)diphenylsilane 
• 1185750-24-6 (3S,4S,5S,6S)-7-(tert-butyldiphenylsilyloxy)-5-(4-methoxybenzyloxy)-4,6-dimethyl-1-(trimethylsilyl)hept-1-yn-3-ol 
• 1044739-29-8 (2S,3R,4S)-3-(4-methoxybenzyloxy)-2,4-dimethylhex-5-en-1-ol 
• 522665-66-3 (3Z,5S,6S,7R,8R,9S,11Z,13S,14R,15S)-8,14-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-16-[(4-methoxyphenyl)methoxy]-5,7,9,11,13,15-hexamethyl-1,3,11-hexadecatrien-6-carbamate 
• 522665-65-2 (3Z,5S,6S,7S,8R,9S,11Z,13S,14R,15S)-6-carbamate-14-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-16-[(4-methoxyphenyl)methoxy]-5,7,9,11,13,15-hexamethyl-1,3,11-hexadecatrien-6,8-diol 
• 522665-58-3 (3Z,5S,6S,7S,9S,11Z,13S,14R,15S)-14-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-hydroxy-16-[(4-methoxyphenyl)methoxy]-5,7,9,11,13,15-hexamethyl-1,3,11-hexadecatrien-8-one 
• 522665-63-0 (3Z,5S,6S,7R,9S,11Z,13S,14R,15S)-14-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-hydroxy-16-[(4-methoxyphenyl)methoxy]-5,7,9,11,13,15-hexamethyl-1,3,11-hexadecatrien-8-one 

Relevant academic research and scientific papers

Total synthesis of discodermolide: Optimization of the effective synthetic route

An efficient and modulable total synthesis of discodermolide (DDM), a unique marine anticancer polyketide is described including related alternative synthetic approaches. Particularly notable is the repeated application of a crotyltitanation reaction to yield homoallylic (Z)-O-ene-carbamate alcohols with excellent selectivity. Advantage was taken of this reaction not only for the stereocontrolled building of the syn-anti methyl-hydroxy- methyl triads of DDM, but also for the direct construction of the terminal (Z)diene. Of particular interest is also the installation of the C13=C14 (Z)-double bond through a highly selective dyotropic rearrangement. The preparation of the middle C8-C14 fragment in two sequential stages and its coupling to the C1-C7 moiety was a real challenge and required careful optimization. Several synthetic routes were explored to allow high and reliable yields. Due to the flexibility and robust character of this approach, it might enable a systematic structural variation of DDM and, therefore, the elaboration and exploration of novel discodermolide structural analogues.

Synthetic studies toward cytostatin, a natural product inhibitor of protein phosphatase 2A

Synthetic approaches toward the natural product cytostatin, an inhibitor of protein phosphatase 2A possessing cytotoxic and antimetastatic activities, have been investigated. A formal synthesis of cytostatin has been achieved according to a strategy relyi

Formal synthesis of (+)-discodermolide.

[structure: see text] Herein we report the formal total synthesis of (+)-discodermolide in 21 steps (longest linear sequence) from commercially available Roche ester. This synthesis features the assembly of C(9-18) and C(19-24) fragments via a metal-chelated aldol coupling reaction.