756524-03-5Relevant academic research and scientific papers
Practical synthesis of β-acyl and β-alkoxycarbonyl heterocyclic sulfones
Pospisil, Jiri,Sato, Hitoshi
, p. 2269 - 2272 (2011)
A short and efficient synthesis for β-acyl and β-alkoxycarbonyl heterocyclic sulfones containing benzothiazol (BT) and phenyltetrazol (PT) heterocyclic core is presented here. The method seems to be general and provides the desired C-nucleophiles in very good to excellent yields from readily available starting materials.
Ring-closing metathesis approaches towards the total synthesis of rhizoxins
Altmann, Karl-Heinz,Liniger, Marc,Neuhaus, Christian M.
supporting information, (2020/10/18)
Efforts are described towards the total synthesis of the bacterial macrolide rhizoxin F, which is a potent tubulin assembly and cancer cell growth inhibitor. A significant amount of work was expanded on the construction of the rhizoxin core macrocycle by ring-closing olefin metathesis (RCM) between C(9) and C(10), either directly or by using relay substrates, but in no case was ringclosure achieved. Macrocycle formation was possible by ring-closing alkyne metathesis (RCAM) at the C(9)/C(10) site. The requisite diyne was obtained from advanced intermediates that had been prepared as part of the synthesis of the RCM substrates. While the direct conversion of the triple bond formed in the ring-closing step into the C(9)-C(10) E double bond of the rhizoxin macrocycle proved to be elusive, the corresponding Z isomer was accessible with high selectivity by reductive decomplexation of the biscobalt hexacarbonyl complex of the triple bond with ethylpiperidinium hypophosphite. Radical-induced double bond isomerization, full elaboration of the C(15) side chain, and directed epoxidation of the C(11)-C(12) double bond completed the total synthesis of rhizoxin F.
Fluorinated 1-phenyl-1H-tetrazol-5-yl sulfone derivatives as general reagents for fluoroalkylidene synthesis
Ghosh, Arun K.,Zajc, Barbara
supporting information; experimental part, p. 8531 - 8540 (2009/12/30)
(Figure Presented) Julia - Kocienski olefination reagents 1-fluoropropyl, (cyclopropyl)fluoromethyl, 1-fluoro-2-methyl-2-propenyl, and 1-fluoro-5-hexenyl 1-phenyl-1H-tetrazol-5-yl (PT) sulfones were prepared by metalation followed by electrophilic fluorin
Total synthesis of the salicylate enamide macrolide oximidine III: Application of relay ring-closing metathesis
Wang, Xiang,Bowman, Emma Jean,Bowman, Barry J.,Porco Jr., John A.
, p. 3601 - 3605 (2007/10/03)
The vacuolar-type (H+)-adenosine triphosphatase inhibitor oximidine III and its enamide and epoxide stereoisomers have been synthesized enantioselectively. A relay ring-closing metathesis (RCM) strategy was employed to facilitate the macrocycli
