（-）-卡利西菲林N的全合成。
Total synthesis of (-)-calyciphylline N.
作者信息
Shvartsbart Artem, Smith Amos B
机构信息
Department of Chemistry, Laboratory for Research on the Structure of Matter, and Monell Chemical Senses Center, University of Pennsylvania , Philadelphia, Pennsylvania 19104, United States.
出版信息
J Am Chem Soc. 2014 Jan 22;136(3):870-3. doi: 10.1021/ja411539w. Epub 2013 Dec 9.
Abstract
The total synthesis of the architecturally complex Daphniphyllum alkaloid (-)-calyciphylline N has been achieved. Highlights of the synthesis include a Et2AlCl-promoted, highly stereoselective, susbtrate-controlled intramolecular Diels-Alder reaction, a transannular enolate alkylation, an effective Stille carbonylation/Nazarov cyclization sequence, and a high-risk diastereoselective hydrogenation of a fully substituted conjugated diene ester.
摘要
结构复杂的虎皮楠生物碱（-）-calyciphylline N的全合成已实现。该合成的亮点包括：二乙基氯化铝促进的、高度立体选择性的、底物控制的分子内狄尔斯-阿尔德反应；跨环烯醇盐烷基化反应；有效的施蒂勒羰基化/纳扎罗夫环化序列；以及对完全取代的共轭二烯酯进行的高风险非对映选择性氢化反应。
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