7020-80-6Relevant articles and documents
Brinton
, p. 1339 (1960)
SILYLATED AZULENYL NITRONE SPIN TRAPS AS CHROMOTROPIC SUPEROXIDE DETECTORS
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Page/Page column 38, (2013/05/22)
Silylated nitrones and methods of detecting and/or superoxide using silylated nitrones are disclosed herein.
Total synthesis of amiclenomycin, an inhibitor of biotin biosynthesis.
Mann, Stephane,Carillon, Sophie,Breyne, Olivier,Marquet, Andree
, p. 439 - 450 (2007/10/03)
We describe the first synthesis of amiclenomycin, a natural product that has been found to inhibit biotin biosynthesis and, as a consequence, to exhibit antibiotic properties. Structure 1, with a trans relationship between the ring substituents. had previously been proposed for amiclenomycin on the basis of its 1H NMR spectrum. We have prepared the trans and cis isomers 1 and 2 by unequivocal routes and we conclude that the natural product is in fact the cis isomer 2. The properly substituted cyclohexadienyl rings were constructed first. A cycloaddition reaction between 1,2-di(phenylsulfonyl)ethylene and the N-allyloxycarbonyl diene 13, followed by reductive elimination of the phenylsulfinyl groups, gave the cis isomer 15. To obtain the trans isomer, the O-trimethylsilyl diene was used to give the cis hydroxylated Diels-Alder adduct 33, which was transformed into the corresponding trans amino derivative by means of a Mitsunobu reaction. The L-alpha-amino acid functionality was introduced by means of a Strecker reaction on the aldehydes 16 and 42, followed by enzymatic hydrolysis with immobilised pronase.