123506-06-9Relevant academic research and scientific papers
THE PYRANOSIDIC HOMOLOGATION ROUTE TO THE NINE CONTIGUOUS CHIRAL CENTERS OF STREPTOVARICIN A1
Mootoo, David R.,Fraser-Reid, Bert
, p. 185 - 200 (2007/10/02)
A precursor for the ansa chain of streptovaricin A has been prepared by means of the pyranosidic homologation strategy.All of the nine contiguous asymmetric centers have been assembled, their authenticity being established by simple 1H NMR methods.The ter
The Nine Contiguous Chiral Centers in Streptovaricin A via Pyranosidic Homologation
Mootoo, David R.,Fraser-Reid, Bert
, p. 5548 - 5550 (2007/10/02)
A tripyranoside 2 has been prepared whose 10-carbon chain is folded so as to afford mutual internal protection of acetal groups.A cis-anti-trans-stereosurface is thereby provided which allows for stereocontrolled development of eight of the nine contiguous asymmetric centers of the ansa chain of streptovaricin A.The "upper" acetal ring is cleaved, and the ninth stereocenter is installed in intermediate 10 by using acyclic stereocontrol principles.The remaining acetal is then opened, and the functional groups exposed thereby are manipulated.All nine stereocenters are created with high stereoselectivity, and the termini of the resulting array, 14b, are suitably differentiated for eventual coupling with the pseudoaromatic residue.
