61999-29-9Relevant academic research and scientific papers
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.
Rhizoxin synthetic studies. 2. Synthesis of the left hand [C(10) to C(19)] and polyene fragments
Provencal, David P.,Gardelli, Cristina,Lafontaine, Jennifer A.,Leahy, James W.
, p. 6033 - 6036 (2007/10/02)
The syntheses of the central core and the polyene fragments of the antitumor macrolide rhizoxin have been achieved in an efficient manner. The core has been prepared in enantiopure form via a asymmetric allylation/aldol protocol. The selective oxidation o
2-OXAZOLINES FROM AMIDES VIA IMIDATES
Meyers, A. I.,Hanagan, Mary Ann,Mazzu, Arthur L.
, p. 361 - 367 (2007/10/02)
Chiral oxazolines useful in asymmetric synthesis of o-substituted phthalides and benzoic acids are readily prepared from the benzamides via their imino ethers.
