187269-86-9Relevant articles and documents
Studies of mild dehydrogenations in heterocyclic systems
Williams, David R.,Lowder, Patrick D.,Gu, Yu-Gui,Brooks, Dawn A.
, p. 331 - 334 (1997)
The use of bromotrichloromethane-DBU is described for the selective oxidative conversion of several dihydro-heterocyclic systems to the corresponding heteroaromatics. Oxidative dehydrogenations to afford 4-hydroxy-2-pyridinones are examined under a variety of conditions. Studies of phenylselenenylation and peracid oxidation provide the novel spirocyclic oxirane 10.
Towards a total synthesis of ulapualide A. Concise synthetic routes to the tris-oxazole ring system and tris-oxazole macrolide core in ulapualides, kabiramides, halichondramides, mycalolides and halishigamides
Chattopadhyay, Shital K.,Kempson, James,McNeil, Alan,Pattenden, Gerald,Reader, Michael,Rippon, David E.,Waite, David
, p. 2415 - 2428 (2007/10/03)
A range of methods for the synthesis of mono-, bis- and tris-2,4-disubstituted oxazoles were evaluated, which led ultimately to a concise synthesis of the three contiguous oxazole ring system 26 in the ulapualide family of 25-membered macrolides, e.g. 1, found in marine organisms. The tris-oxazole macrolide core 30 in ulapualide A (1) was also synthesised based on a macrolactamisation strategy from the two functionalised mono-oxazole precursors 28 and 29, followed by oxazoline 45 and oxazole ring formation, exploiting the methodologies established in the synthesis of linear bis- and tris-oxazoles in the formation of 18 and 26. The tris-oxazole 26 was converted into the corresponding phosphonium salt 5 in readiness for elaboration to ulapualide A (1). The Royal Society of Chemistry 2000.
