Pot and time economies in the total synthesis of Corey lactone
Nariyoshi Umekubo1, Yurina Suga1, Yujiro Hayashi1
1Department of Chemistry, Graduate School of Science, Tohoku University Sendai 980-8578 Japan yujiro.hayashi.b7@tohoku.ac.jp.
Abstract:
The Corey lactone is a highly versatile intermediate for the synthesis of a variety of prostaglandin hormones that natively control a multitude of important physiological processes. Starting from commercially available compounds, we herein disclose a time-economical, one-pot enantioselective preparation of the Corey lactone by virtue of a new diphenylprolinol silyl ether-mediated domino Michael/Michael reaction to afford the substituted cyclopentanone core in a formal (3 + 2) cycloadditive fashion. More broadly, this work advances the on-demand, gram-scale synthesis of high-value targets involving chemically orthogonal transformations, whereby distinct reactions of acids, bases, organometalics, reductants and oxidants can be carried out in a single reaction vessel in a sequential fashion.
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