143236-76-4Relevant academic research and scientific papers
Total Synthesis of Ionomycin Using Ring-Opening Strategies
Lautens, Mark,Colucci, John T.,Hiebert, Sheldon,Smith, Nicholas D.,Bouchain, Giliane
, p. 1879 - 1882 (2007/10/03)
(Matrix Presented) The total synthesis of the polyether antibiotic ionomycin, a calcium ionophore, is described. The synthesis demonstrates the utility of ring-opening methodologies as applied to the synthesis of polypropionate and deoxypolypropionate subunits, which are found in two of the four fragments in the synthesis.
Synthesis of salinomycin
Kocienski, Philip J.,Brown, Richard C. D.,Pommier, Agnes,Procter, Martin,Schmidt, Bernd
, p. 9 - 40 (2007/10/03)
Salinomycin, a commercially significant coccidiostat isolated from Streptomyces albus, has been synthesised from three principal fragments.Key steps include (a) the use of η3-allylmolybdenum cationic complexes 21a,b for the stereoselective construction of two contiguous stereogenic centres in fragment 5a; (b) the electrophilic cyclisation of 2-(prop-2-ynyl)-2-hydroxyoxanes to give molybdenum and chromium carbene complexes which are precursors to the furan fragment 7; (c) the diastereoselective oxidation of a 1,5-diene with potassium permanganate to generate four stereogenic centres in a single step leading to fragment 8; (d) the oxidative rearrangement of acylfuran 89 en route to the 1,6,8-trioxadispiropentadec-13-ene dispiroacetal core; and finally (e) the use of an allenol ether as an acyl anion equivalent together with the stereoselective hydrolysis of allenol ether intermediate 112 in an alternative synthesis of the dispiroacetal core.
Synthetic Investigations of Rapamycin. 1. Synthesis of a C10-C21 Fragment
Meyer, Stephanie D.,Miwa, Tetsuo,Nakatsuka, Masashi,Schreiber, Stuart L.
, p. 5058 - 5060 (2007/10/02)
Phosphine oxide 2, representing the C10-C21 portion of rapamycin, was stereoselectively synthesized and was demonstrated to undergo a Horner-Wittig reaction to form triene 25 as an 8:1 mixture of trans-cis isomers.
