ORGN 569 |
Asymmetric binaphthyl coupling en route to cercosporin
| Carol A. Mulrooney and Marisa C. Kozlowski. Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA 19104 |
| Chiral 1,5-diaza-cis-decalins are effective ligands in the copper catalyzed asymmetric biaryl coupling reaction. Highly functionalized naphthalenes can be united to provide binaphthalenes with good enantioselectivity. This method is being utilized to construct advanced intermediates for the asymmetric total syntheses of the perylenequinone natural products. Progress toward the total synthesis of cercosporin will be reported. Specifically, investigations to install the C7/C7' alkyl substituents, to oxidize the C5/C5' carbons, to decarboxylate the C3/C3' positions, and to form the seven-membered ring will be discussed. 
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