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Preparation of optically active functionalized cis delta 6 1 octalones


, : Preparation of optically active functionalized cis delta 6 1 octalones. Journal of Organic Chemistry 50(11): 1904-1911

A preparation of optically pure, functionalized cis-.DELTA.6-1-octalones starting with (-)-.beta.-pinene (92% ee) is detailed. The conversion of (-)-.beta.-pinene to (-)-cis-nopinol (> 97% ee) and its utilization in the preparation of (4R,9R,10R)-(+)-4-(acetylamino)-9-(methoxycarbonyl)-cis-.DELTA.6-1-octalone ethylene ketal (1), a cis-.DELTA.6-1-octalone possessing the correct absolute configuration at 3 appropriately functionalized chiral centers characteristic of the morphine-related analgesics, is described.

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