✍ Scribed by Robert M. Carlson; Alan R. Oyler
No coin nor oath required. For personal study only.
The use of a nucleophilic acyl equivalent is the basis of several valuable synthetic methods.' Acetylides potentially represent such acyl synthons if advantage could be taken of a regiospecific hydration procedure (Eqn. 1). The nucleophilic properties of propiolic acid dianion(1) have therefore been evaluated for this purpose on the basis of predicted susceptibility of the 8 carbon of the conjugated product towards nucleophilic attack (Eqn. 2).2y3
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A convenient synthesis of 3-cl'-hydroxyethyl)-2-azetldlnone-4-yl acetic acid, one of the key IntermedIates I" the thlenamycin total synthesis, based on the chemistry of the dlanlon derived from readily avallable Z-azetidlnone-4-yl acetic acid 1s described Recently, a practical synthesis of (?)-thien
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