Synthesis 2003(13): 2041-2046
DOI: 10.1055/s-2003-41004
PAPER
© Georg Thieme Verlag Stuttgart · New York

An Efficient Synthetic Strategy for Geometrically Pure Symmetrical and Unsymmetrical Hydroxystilbenes via McMurry Coupling

Narayan V. Mayekar, Subrata Chattopadhyay*, Sandip K. Nayak
Bio-Organic Division, Bhabha Atomic Research Centre, Mumbai - 400 085, India
Fax: +91(22)25505151; e-Mail: schatt@apsara.barc.ernet.in ;
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Publikationsverlauf

Received 9 April 2003
Publikationsdatum:
07. August 2003 (online)

Abstract

Intramolecular reductive deoxygenation of ethylenedioxy tethered symmetrical and unsymmetrical aromatic bis(carbon­yl) ethers with the low-valent titanium (LVT) reagent (TiCl4-Zn-THF) yielded chromatographically separable E/Z-isomers of corresponding cyclic stilbenes which were further dealkylated to obtain geometrically pure hydroxystilbenes. The intramolecular McMurry coupling of the tethered bis(carbonyl) ethers with TiCl3-Li-THF, on the other hand, directly provided both symmetrical and unsymmetrical phenanthrenes via in situ dealkoxylation of the phenol function. This is the first report of the synthesis of unsymmetrical phenanthrenes by the LVT route.