From Central to Axial to Central Chirality: Enantioselective Construction of the trans‐4,5,9,10‐Tetrahydroxy‐9,10‐dihydrophenanthrene System

Medientyp: E-Artikel
Titel: From Central to Axial to Central Chirality: Enantioselective Construction of the trans‐4,5,9,10‐Tetrahydroxy‐9,10‐dihydrophenanthrene System
Beteiligte: Stavrakov, Georgi; Keller, Manfred; Breit, Bernhard
Erschienen: Wiley, 2007
Erschienen in: European Journal of Organic Chemistry
Sprache: Englisch
DOI: 10.1002/ejoc.200700583
ISSN: 1434-193X; 1099-0690
Schlagwörter: Organic Chemistry ; Physical and Theoretical Chemistry
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Beschreibung: <jats:title>Abstract</jats:title><jats:p>Enantioselective synthesis of the core <jats:italic>trans</jats:italic>‐4,5,9,10‐tetrahydroxy‐9,10‐dihydrophenanthrene parent system of the antibiotics benanimicin, pradimicin and FD 594 has been accomplished. The synthesis employs a chiral tether approach and makes use of efficient central to axial to central chirality transfer. Key to success was an “imine‐directed” atropdiastereoselective Ullmann coupling under mild reaction conditions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)</jats:p>

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