The total synthesis of the diepoxycyclohexanone antibiotic aranorosin and novel synthetic analogues

Autor:	Richard J. K. Taylor, Lewis Norman John, Lee McLaren, Alexander McKillop, Robert John Watson
Rok vydání:	1996
Předmět:	Hydroxylation chemistry.chemical_compound chemistry Stereochemistry Natural compound Hypervalent molecule Total synthesis Aranorosin Combinatorial chemistry Derivative (chemistry)
Zdroj:	Journal of the Chemical Society, Perkin Transactions 1. :1385
ISSN:	1364-5463 0300-922X
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::ff84b44ca09b405f3f7e5f24ac27eb3e https://doi.org/10.1039/p19960001385 Zobrazit plný text záznamu