I. K. Sagamanova, V. V. Tumanov, W. A. Smit, G. V. Zatonsky, “Preparation of linearly fused 6-6-5 and 6-5-5 carbotricyclic ring systems related to the natural polyquinanes”, Mendeleev Commun., 2008, Volume 18, Issue 4,Pages <nobr>203

This article is cited in 3 papers

Preparation of linearly fused 6-6-5 and 6-5-5 carbotricyclic ring systems related to the natural polyquinanes

I. K. Sagamanova^a, V. V. Tumanov^b, W. A. Smit^b, G. V. Zatonsky^b

^a Higher Chemical College of the Russian Academy of Sciences, D.I. Mendeleev University of Chemical Technology of Russia, Moscow, Russian Federation
^b N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation

Abstract: A short pathway to the formation of the title framework is elaborated via (i) the tandem addition of arylsulfenium chloride and 1-siloxycycloalkenes across the double bond of dicobalthexacarbonyl complex of vinylacetylene, (ii) the diastereoselective Grignard reaction at the carbonyl group of the formed adducts; and (iii) the Pauson–Khand cyclization of 1,6- or 1,7-enyne precursors thus prepared.

Keywords: 6-6-5 tricyclics, 6-5-5 tricyclics, Pauson-Khand cyclization, one-pot reaction.

Language: English

DOI: 10.1016/j.mencom.2008.07.011