Pot and time economies in the total synthesis of Corey lactone,Chemical Science

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Pot and time economies in the total synthesis of Corey lactone
Chemical Science ( IF 7.6 ) Pub Date : 2019/12/23 , DOI: 10.1039/c9sc05824a
Nariyoshi Umekubo ₁ , Yurina Suga ₁ , Yujiro Hayashi ₁

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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.

中文翻译：

科里内酯全合成中的罐头经济和时间经济

Corey 内酯是一种用途广泛的中间体，可用于合成多种天然控制多种重要生理过程的前列腺素激素。从市售化合物开始，我们在此公开了一种时间经济的、一锅法的 Corey 内酯的对映选择性制备方法，该方法是利用新的二苯基脯氨醇甲硅烷基醚介导的多米诺 Michael/Michael 反应以形式 (3 + 2) 环加成方式。更广泛地说，这项工作推进了涉及化学正交转化的高价值目标的按需、克级合成，由此酸、碱、有机金属、还原剂和氧化剂的不同反应可以在单个反应容器中按顺序进行时尚。

更新日期：2020-02-13

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