Journal of the Chemical Society. Perkin transactions I p. 1385 - 1393 (1996)
Update date:2022-07-30
Topics:
McKillop, Alexander
McLaren, Lee
Taylor, Richard J. K.
Watson, Robert J.
Lewis, Norman J.
A short synthesis of the novel antibiotic aranorosin in chiral form is described which employs (i) a novel hypervalent iodine-mediated oxidative hydroxylation of a tyrosinal derivative and (ii) a stereocontrolled cis-bisepoxidation in the key steps. A similar procedure was employed to prepare 6′-epiaranorosin, and hence establish the stereochemistry of the natural compound, and to prepare novel aranorosin analogues. An organometallic route is described which gives desamidoaranorosin.
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