213740-06-8

Upstream product

• 213740-16-0 ethyl (Z,4R)-6-[1-(tert-butyl)-1,1-diphenylsilyl]oxy-2-ethyl-4-methyl-2-hexenoate 
• 1322669-19-1 C₂₉H₃₈O₃Si 
• 1322669-25-9 C₁₃H₂₀O₃ 
• 914641-63-7 1-methoxy-4-([(2R)-2-methyl-3-butenyl]oxymethyl)benzene 
• 410523-57-8 (2'S,2R)-(-)-1'-(4-tert-butyldiphenylsilyloxy-2-methyl-1-butylidenamino)-2'-(methoxymethyl)pyrrolidine 
• 410523-50-1 (S)-(-)-1'-(4-tert-butyldiphenylsilyloxy-1-butylidenamino)-2'-(methoxymethyl)pyrrolidine 
• 2938-98-9 (R)-2-methylbutane-1,4-diol 
• 127793-62-8 4-((tert-butyldiphenylsilyl)oxy)butanal 
• 3641-51-8 2-(R)-methylsuccinic acid 
• 213740-15-9 (2R)-4-[1-(tert-butyl)-1,1-diphenylsilyl]oxy-2-methylbutan-1-ol 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 126616-47-5 (R)-(-)-4-tert-butyldiphenylsilyloxy-1-methylbutanal 
• 118715-16-5 4-((tert-butyldiphenylsilyl)oxy)butanoic acid 
• 131216-52-9 4-(tert-butyl(diphenyl)silanyloxy)butyryl chloride 

Downstream Products

• 410523-53-4 (2'R,6'R,1E,3Z,5R)-(+)-7-tert-butyldiphenylsilyloxy-1-(5',6'-dihydro-2'H-2'-isopropoxypyran-6'-yl)-3-ethyl-5-methylhepta-1,3-diene 
• 1322669-26-0 C₂₅H₃₄O₂Si 
• 1322669-20-4 tert-butyl [(3R,4Z)-5-ethyl-3-methyl-4,6-heptadienyl]oxydiphenylsilane 
• 213740-17-1 (3Z,5R)-(+)-3-bromomethyl-7-tert-butyldiphenylsilyloxy-5-methylhept-3-ene 

Relevant academic research and scientific papers

Studies towards the total synthesis of (-)-callystatin A

The synthesis of C1-C12 and C13-C 22 fragments of (-)-callystatin A is accomplished employing desymmetrization strategy for the creation of five chiral centres of the polypropionate fragment and application of c

A practical synthesis of (-)-kazusamycin A (revised)

We describe herein a stereo-controlled and practical synthesis of three key building blocks, namely Segment AB′, Segment D, and Segment E′ needed for the total synthesis of (-)-kazusamycin A.

Asymmetric total synthesis of (-)-callystatin A and (-)-20-epi-callystatin A employing chemical and biological methods

An efficient asymmetric total synthesis of the potent cytotoxic marine natural product (-)-callystatin A and its 20-epi analogue has been achieved. The synthetic pathway involved the preparation of three fragments to be coupled with each other at the end of the route. The first fragment 3 was obtained using a biocatalytic enantioselective reduction of a 3,5-dioxocarboxylate as the key step. For the second intermediate 4 the asymmetric α-alkylation of an O-protected derivative of 4-hydroxybutanal was performed exploiting the SAMP/ RAMP hydrazone alkylation methodology, and followed by a highly Z-selective Homer-Wadsworth-Emmons reaction under modified conditions. For the synthesis of the polypropionate fragment 5 a diastereoselective syn-aldol reaction was employed between a chiral ethyl ketone and an α-substituted chiral aldehyde, both prepared in enantiopure form again by means of the asymmetric alkylation of their corresponding RAMP hydrazones. Finally, these three building blocks were coupled using highly E-selective Wittig reactions via allyltributylphosphonium ylides to afford the target compounds after a final oxidation/deprotection sequence.

Oxabicyclo[3.2.1]oct-6-enes as templates for the stereoselective synthesis of polypropionates: Total synthesis of callystatin a and C19-epi-callystatin A

The total synthesis of the polyketide natural product callystatin A and its novel analog C19-epi-callystatin A is described. Our strategy features the use of an enantiomerically pure oxabicyclo[3.2.1]oct-6-ene as a template for the stereocontrolled preparation of the C15-C21 polypropionate region.

Asymmetric total synthesis of (-)-callystatin A employing the SAMP/RAMP hydrazone alkylation methodology

(equation presented) The asymmetric total synthesis of (-)-callystatin A has been achieved. The key steps generating the stereogenic centers rely on the asymmetric α-alkylation of aldehydes or ketones exploiting the SAMP/RAMP hydrazone alkylation methodology, as well as an enzymatic enantioselective reduction of a 3,5-dioxocarboxylate. For the construction of the alkene moieties, highly selective Wittig or Horner-Wadsworth-Emmons reactions were employed.