(-)-变异林和(-)-甘醇的不对称全合成。
Asymmetric total syntheses of (-)-variabilin and (-)-glycinol.
机构信息
Department of Chemistry, Wesleyan University, Middletown, Connecticut 06459, USA.
出版信息
Org Lett. 2011 Jul 15;13(14):3686-9. doi: 10.1021/ol201332u. Epub 2011 Jun 13.
Abstract
Total syntheses of (-)-variabilin and (-)-glycinol have been accomplished, using the catalytic, asymmetric "interrupted" Feist-Bénary reaction (IFB) as the key transformation to introduce both stereogenic centers. A monoquinidine pyrimidinyl ether catalyst affords the IFB products in over 90% ee in both cases. Other key steps include an intramolecular Buchwald-Hartwig coupling and a nickel-catalyzed aryl tosylate reduction.
摘要
(-)-变葫芦素和(-)-甘氨醇的全合成已经完成，使用催化、不对称的“中断”费斯特-本纳反应（IFB）作为关键转化来引入两个手性中心。单奎宁嘧啶基醚催化剂在两种情况下都能以超过 90%的对映体过量值（ee）提供 IFB 产物。其他关键步骤包括分子内 Buchwald-Hartwig 偶联和镍催化的芳基对甲苯磺酸盐还原。
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