S. E. Macwhorter, N. Schore
1991
Citations
0
Influential Citations
11
Citations
Journal
Journal of Organic Chemistry
Abstract
A 10-step sequence is described for the conversion of 4-methyl-exo-tricyclo [5.2.1.0 2,6 ] deca-4,8-dien-one (the Pauson-Khand cycloaddition product of norbornadiene with propyne) into 3,3-dimethyl-2-[(2-methoxyethoxy) methoxy]-8-(1-methyl-2-oxopropyl) bicyclo [3.3.0] octan-6-ol. The latter diquinane, formed with complete stereocontrol and well-differentiated functionality, is appropriately substituted to serve as an entry to highly functionalized linearly fused triquinanes, although attempts to close a third five-membered ring via an enolate-epoxide ring-opening proces were unsucessful