Studies are proposed in which aromatic oxazolines (phenyl, naphthyl) are utilized to introduce, in a stereospecific manner, two or more chiral centers into the aromatic ring. With the appropriate choice of nucleophiles and trapping electrophiles, we hope to reach a variety of important naturally occurring biologically active systems. This study will provide access to (+)-compactin, (+)-aklavinone, (-)-podophyllotoxin, 11-ketosteroids, (+)-steganone, and key intermediates for the synthesis of chlorothricolide, lasalocid A, as well as cavity compounds. Furthermore, heterocyclic aromatics containing oxazolines will be studied to introduce substituents, enantioselectively, into the pyridine and quinoline rings. The products of these reactions will provide access to nefidipine, streptonigrin, and chiral binaphthyls where one ring system is quinoline. Earlier reported studies from this laboratory provide the basis for the above goals.
