BIOLOGICALLY ACTIVE COMPOUNDS VIA CHIRAL AROMATICS

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Continued studies on the addition to chiral naphthalenes by a variety of organometallics will provide a host of novel chiral non-racemic dihydronaphthalenes with two newly inserted stereocenters. Viable routes using this methodology will lead to the aphidocolin, scopudulcic acid and kaurane skeletons in efficient yields. Although the approach to the final natural materials is desirable, it is not deemed as the only goal of this program. Understanding of the method and scope to reach a wide variety of chiral systems is the primary goal. In addition to the above, it is also likely that an efficient asymmetric route to 11 -keto steroids will emerge, as well as abietic acid derivatives (Taxodione) and other related systems. These can be accessed via intramolecular tandem additions. Work is also planned to reach additional chiral biaryls by coupling aryl Grignard reagents with aryl oxazolines. This has already proven its value in earlier synthetic achievements. The last portion of this study will concentrate on continuing our effort to design a chiral NADH-mimic, already successful on a stoichiometric level. We will attempt to make this process catalytic to truly mimic the natural reduction of imines to amino acids, and ketoacids to lactates.