Diastereoselective intramolecular Friedel-Crafts alkylation of tetralins |
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Authors: | Liébert Clémence Brinks Marion K Capacci Andrew G Fleming Matthew J Lautens Mark |
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Affiliation: | Davenport Chemical Laboratories, Department of Chemistry, University of Toronto, 80 St George Street, Toronto, Ontario M5S 3H6, Canada. |
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Abstract: | An efficient and versatile synthesis of cis-hexahydrobenzophenanthridines starting from readily available tetralins has been developed using an intramolecular Friedel-Crafts alkylation as a key step. The substrates were prepared via a highly stereocontrolled rhodium-catalyzed ring-opening reaction of meso-oxabicyclic alkenes and a hydrogenation sequence. Thus, a wide variety of complex tetracyclic compounds have been isolated with a high level of regio-, diastereo-, and enantioselectivity. |
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