139517-64-9Relevant academic research and scientific papers
Total synthesis of the vancomycin aglycon
Boger, Dale L.,Miyazaki, Susumu,Kim, Seong Heon,Wu, Jason H.,Castle, Steven L.,Loiseleur, Olivier,Jin, Qing
, p. 10004 - 10011 (2007/10/03)
Full details of a diastereoselective total synthesis of the vancomycin aglycon are described. Two key aromatic nucleophilic substitution macrocyclizations with formation of the 16-membered diaryl ethers were enlisted for sequential CD and DE ring formations, an effective macrolactamization was developed for closure of the 12-membered biaryl AB ring system, and the defined order of CD, AB, and DE ring closures permitted selective thermal atropisomerism of the newly formed ring systems or their immediate precursors. This indirect control of the atropisomer stereochemistry allowed all synthetic material to be funneled into the one of eight atropdiastereomers characterizing the natural product.
Application of the Suzuki Biphenyl Synthesis to the Natural Products Biphenomycin and Vancomycin
Brown, Allan G.,Crimmin, Michael J.,Edwards, Peter D.
, p. 123 - 130 (2007/10/02)
The synthesis of the unsymmetrical biphenyls 10 and 25 has been carried out by the palladium(0) catalysed coupling of the aryl boronic derivatives 5 and 20 with the aryl bromides 9 and 23 derived from (R)-4-hydroxyphenylglycine and (S)-tyrosine.In the former case unsuccessful attempts were made to bring about cyclization to compound 4 which is an analogue of the biphenyl ring system found in vancomycin.In the latter case, a variety of cyclization methods were used to give the cyclic products 34 and 35 which are analogues of the biphenomycin antibiotics.
