725715-24-2Relevant academic research and scientific papers
Synthesis, conformational preferences, and biological activity of conformational analogues of the microtubule-stabilizing agents, (-)-zampanolide and (-)-dactylolide
Henry, Jeffrey L.,Wilson, Matthew R.,Mulligan, Michael P.,Quinn, Taylor R.,Sackett, Dan L.,Taylor, Richard E.
supporting information, p. 800 - 805 (2019/05/29)
Zampanolide and dactylolide are microtubule-stabilizing polyketides possessing potent cytotoxicity towards a variety of cancer cell lines. Using our understanding of the conformational preferences of the macrolide core in both natural products, we hypothe
Enantioselective Modular Total Synthesis of Macrolides Sch725674 and C-4-epi-Sch725674
Sharma, Brijesh M.,Gontala, Arjun,Kumar, Pradeep
, p. 1215 - 1226 (2016/03/05)
The convergent total synthesis of Sch725674 has been accomplished by starting from (R)-1,2-epoxyheptane and assembling five modules in a highly stereoselective manner to give the final product in 6.6 % overall yield. The same strategy was extended to the
A concise and efficient stereoselective synthesis of the C1-C11 fragment of macrolactin A
Bonini, Carlo,Chiummiento, Lucia,Videtta, Valeria,Colobert, Fran?oise,Solladié, Guy
, p. 2427 - 2430 (2008/02/10)
A stereoselective synthesis of the C1-C11 fragment of macrolactin A, using original approaches for the introduction of the Z,E-diene stereochemistry and the C-7 stereogenic center, is reported. The adopted strategy has allowed us to build up the fragment
Synthesis of the EF-ring segment of ciguatoxin CTX1B based on novel regioselective reduction of unsaturated cyanohydrins and ring-closing olefin metathesis
Takemura, Atsushi,Fujiwara, Kenshu,Shimawaki, Ken,Murai, Akio,Kawai, Hidetoshi,Suzuki, Takanori
, p. 7392 - 7419 (2007/10/03)
Aiming at a convergent total synthesis of ciguatoxin CTX1B, its EF-ring segment has been synthesized. During the synthesis, a novel method for the construction of branched ethers, based on regioselective reduction of γ-alkoxy β,γ-unsaturated α-silyloxy ni
The stereocontrolled total synthesis of altohyrtin A/spongistatin 1: The CD-spiroacetal segment
Paterson, Ian,Coster, Mark J.,Chen, David Y.-K.,Gibson, Karl R.,Wallace, Debra J.
, p. 2410 - 2419 (2007/10/03)
Stereocontrolled syntheses of the C16-C28 CD-spiroacetal subunit of altohyrtin A/spongistatin 1 (1), relying on kinetic and thermodynamic control of the spiroacetal formation, are described. The kinetic control approach resulted in a slight preference (60: 40) for the desired spiroacetal isomer. The thermodynamic approach allowed ready access to the desired spiroacetal 2 by acid-promoted equilibration, Chromatographic separation of the C23 epimers and resubjection of the undesired isomer to the equilibration conditions. This scalable synthetic sequence provided multi-gram quantities of 2, thus enabling the successful completion of the total synthesis of altohyrtin A/spongistatin 1, as reported in Part 4 of this series. The Royal Society of Chemistry 2005.
Stereochemistry of hydrogen removal from the 'unactivated' C-3 position of 4-hydroxybutyryl-CoA catalysed by 4-hydroxybutyryl-CoA dehydratase.
Scott, Richard,Naeser, Ulrike,Friedrich, Peter,Selmer, Thorsten,Buckel, Wolfgang,Golding, Bernard T
, p. 1210 - 1211 (2007/10/03)
(R)- and (S)-gamma-[3-(2)H(1)]butyrolactones have been synthesised from (R)- and (S)-glycidol, respectively, and used to demonstrate that it is the pro-(S) hydrogen atom that is stereospecifically abstracted from C-3 of 4-hydroxybutyryl-CoA by 4-hydroxybu
Studies in marine macrolide synthesis: Synthesis of a C16-C28 subunit of spongistatin 1 (altohyrtin A) incorporating the CD-spisoacetal moiety
Paterson, Ian,Wallace, Debra J.,Gibson, Karl R.
, p. 8911 - 8914 (2007/10/03)
The C16-C28 ketone 3, containing the CD-spiroacetal of spongistatin 1 (1), was prepared in 17 steps from aldehyde 9. Both thermodynamic and kinetic conditions were explored for controlling the CD-acetal configuration.
