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

Stavrakov Georgi | Zendy; Keller Manfred | Zendy; Breit Bernhard | Zendy

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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)

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