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From Central to Axial to Central Chirality: Enantioselective Construction of the trans ‐4,5,9,10‐Tetrahydroxy‐9,10‐dihydrophenanthrene System
Author(s) -
Stavrakov Georgi,
Keller Manfred,
Breit Bernhard
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700583
Subject(s) - enantioselective synthesis , chemistry , imine , chirality (physics) , axial chirality , stereochemistry , total synthesis , combinatorial chemistry , organic chemistry , catalysis , chiral perturbation theory , physics , nambu–jona lasinio model , pion , particle physics
Enantioselective synthesis of the core trans ‐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)