960595-71-5Relevant academic research and scientific papers
Structure-activity relationships of ustiloxin analogues
Joullié, Madeleine M.,Berritt, Simon,Hamel, Ernest
scheme or table, p. 2136 - 2139 (2011/05/09)
Four novel ustiloxin D analogues were synthesized focusing on the size of the macrocyclic core, the stereochemistry at the bridgehead ether, and the enantiomer of ustiloxin D. All four were subjected to biological evaluation testing the inhibition of tubu
Evolution of the total syntheses of ustiloxin natural products and their analogues
Li, Pixu,Evans, Cory D.,Wu, Yongzhong,Cao, Bin,Hamel, Ernest,Joullie, Madeleine M.
, p. 2351 - 2364 (2008/09/20)
Ustiloxins A-F are antimitotic heterodetic cyclopeptides containing a 13-membered cyclic core structure with a synthetically challenging chiral tertiary alkyl-aryl ether linkage. The first total synthesis of ustiloxin D was achieved in 31 linear steps using an SNAr reaction. An NOE study of this synthetic product showed that ustiloxin D existed as a single atropisomer. Subsequently, highly concise and convergent syntheses of ustiloxins D and F were developed by utilizing a newly discovered ethynyl aziridine ring-opening reaction in a longest linear sequence of 15 steps. The approach was further optimized to achieve a better macrolactamization strategy. Ustiloxins D, F, and eight analogues (14-MeO-ustiloxin D, four analogues with different amino acid residues at the C-6 position, and three (9R,10S)-epi-ustiloxin analogues) were prepared via the second-generation route. Evaluation of these compounds as inhibitors of tubulin polymerization demonstrated that variation at the C-6 position is tolerated to a certain extent. In contrast, the S configuration of the C-9 methylamino group and a free phenolic hydroxyl group are essential for inhibition of tubulin polymerization.
A regio- and stereoselective approach to quaternary centers from chiral trisubstituted aziridines
Forbeck, Erin M.,Evans, Cory D.,Gilleran, John A.,Li, Pixu,Joullie, Madeleine M.
, p. 14463 - 14469 (2008/09/17)
A thorough investigation of a regio- and stereospecific aziridine ring opening reaction presents new synthetic technology for the construction of a variety of quaternary β-substituted-α-amino functional groups. Mild, metal-free reaction conditions allow f
