172104-03-9

Upstream product

• 1190042-40-0 C₂₀H₂₈O₄ 
• 1003-14-1 2-pentyloxirane 
• 1158076-88-0 ((2S,3S)-3-(4-(benzyloxy)butyl)oxiran-2-yl)methanol 
• 1374783-95-5 (S)-7-(benzyloxy)hept-1-yn-3-ol 
• 1374783-93-3 [(S)-7-(benzyloxy)hept-1-yn-3-yloxy](tert-butyl)dimethylsilane 
• 1374783-92-2 (4R,8S)-12-(benzyloxy)-8-(tert-butyldimethylsiloxy)dodec-6-yn-4-ol 
• 1374783-96-6 (5S,9R,E)-5-(tert-butyldimethylsiloxy)dodec-6-ene-1,9-diol 
• 1374783-91-1 (5S,9R,E)-5-(tert-butyldimethylsiloxy)-9-hydroxydodec-6-enoic 
• 1374783-97-7 (6S,10R,E)-6-(tert-butyldimethylsiloxy)-10-propyl-3,4,5,6,9,10-hexahydro-2H-oxecin-2-one 
• 1374783-94-4 (2S,3R)-2-[4-(benzyloxy)butyl]-3-(chloromethyl)oxirane 
• 111-29-5 1 ,5-pentanediol 
• 4541-15-5 5-(benzyloxy)-1-pentanol 
• 78999-24-3 5-benzyloxy-1-pentanal 
• 99016-97-4 (E)-7-(benzyloxy)-2-hepten-1-ol 

Relevant academic research and scientific papers

The first chemoenzymatic total synthesis of the phytotoxic nonenolide putaminoxin and its (5S,6E,9S)-diastereomer

The limitations of an alcohol dehydrogenase regarding the oxidative kinetic resolution of homoallylic alcohol containing alkyl chains were investigated, leading to a valuable building block for the total synthesis of phytotoxic nonenolide putaminoxin. The enzymatic approach towards the enantioenriched homoallylic alcohol was compared to classical, nonenzymatic approaches using asymmetric reagent controlled allyl additions and the obtained building block was used for the total synthesis of putaminoxin and its (5S,6E,9S)-diastereomer. After the spectroscopic analysis of the synthesized compounds, discrepancies were observed to already published data of isolated and synthesized putaminoxin. Therefore, a systematic comparison of NMR data was carried out. The result underlines the necessity of total synthesis for the absolute assignment of configuration.

Stereoselective total synthesis of putaminoxin

The stereoselective total synthesis of a phytotoxic macrolide putaminoxin, isolated from the culture of Phoma putaminum fungus, has been accomplished by utilization of Sharpless asymmetric epoxidation, Birch reduction, Jacobsens kinetic resolution of race

Novel synthesis of stagonolide-F, putaminoxin and aspinolide-A

Novel synthesis of putaminoxin, stagonolide-F and aspinolide-A have been achieved by utilizing (S) and (R)- malic acid. The key feature of the synthetic strategy includes Horner-Wittig olefination, double bond reduction and Steglich esterification. Olefinic acid for putaminoxin and stagonolide-F was prepared from (S)-malic acid whereas olefinic acid for aspinolide-A was prepared from (R)-malic acid and olefinic alcohols for putaminoxin, stagonolide-F and aspinolide-A were prepared by using Brown's asymmetric allylboration.

The first total synthesis of putaminoxin and determination of its absolute configuration

Asymmetric synthesis of putaminoxin, a phytotoxic macrolide from the cultured dinoflagellate Amphidinium sp., has been accomplished. Absolute configuration of putaminoxin was concluded to be 1 from comparison of the NMR data and [α]D values of synthetic and natural putaminoxin.