Multigram synthesis of an advanced nitroalkene intermediate: application in synthesis of octahydroindol-2-one derivative featuring diastereoselective Michael addition of diethylmalonate

作者：Bhorkade Shashikant B^*; Gavhane Kishor B

来源：Tetrahedron Letters, 2016, 57(24): 2575-2578.

DOI：10.1016/j.tetlet.2016.04.055

• Nitrocyclohexenetriol
• Diastereoselective Michael addition
• Octahydroindole
• Intramolecular Henry reaction
• Krapcho's decarboxylation

Gram scale synthesis of a novel nitrocyclohexenetriol derivative is reported by applying intramolecular Henry reaction as a key step. Searching the utility of this scaffold, synthesis of hydroxylated octahydroindol-2-one derivative, which is a backbone of many amaryllidaceae alkaloids was also achieved via a very diastereoselective Michael addition of diethylmalonate to hydroxylated nitrocyclohexenetriol.

• 出版日期2016-6-15