123284-89-9Relevant articles and documents
Synthesis and electrochemical studies of new antimalarial endoperoxides
Najjar, Fadia,Baltas, Michel,Gorrichon, Liliane,Moreno, Yolande,Tzedakis, Theodore,Vial, Henri,Andre-Barres, Christiane
, p. 3335 - 3343 (2003)
Structural analogues of endoperoxides belonging to the family of G factors have been synthesized under Mannich-type conditions. The structures of the different diastereoisomers have been established from NMR spectroscopic data. Their cathodic peak potentials have been determined by thin layer electrochemistry under potentiostatic conditions, and compared to artemisinin. These endoperoxides were evaluated in vitro against Plasmodium falciparum and showed moderate to good activity. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
Identification and Total Synthesis of an Unstable Anticancer Macrolide Presaccharothriolide Z Produced by Saccharothrix sp. A1506
Ikeda, Hiroaki,Kakeya, Hideaki,Kuranaga, Takefumi,Nakagawa, Yusuke,Tamura, Miho,Terada, Sakahiro
, p. 7106 - 7111 (2021/09/14)
Saccharothriolides A-F are 10-membered microbial macrolides proposed to be generated from their precursors presaccharothriolides X-Z. Previously, we isolated presaccharothriolide X, and its unique natural prodrug-like properties have intrigued us. However
Ring-closing metathesis approaches towards the total synthesis of rhizoxins
Altmann, Karl-Heinz,Liniger, Marc,Neuhaus, Christian M.
, (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.