Synthesis of (2R,4S)-4-Amino-5-hydroxybicyclo[3.1.1]heptane-2-carboxylic Acid via an Asymmetric Intramolecular Mannich Reaction,The Journal of Organic Chemistry

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Synthesis of (2R,4S)-4-Amino-5-hydroxybicyclo[3.1.1]heptane-2-carboxylic Acid via an Asymmetric Intramolecular Mannich Reaction
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2024-06-10 , DOI: 10.1021/acs.joc.4c00781
Adrian O Dukes ₁ , Pathum M Weerawarna ₂ , Allison N Devitt ₁ , Richard B Silverman ₁

Affiliation

Inhibition of human ornithine aminotransferase interferes with glutamine and proline metabolism in hepatocellular carcinoma, depriving tumors of essential nutrients. A proposed mechanism-based inhibitor containing a bicyclo[3.1.1]heptanol warhead is reported herein. The proposed inactivation mechanism involves a novel α-iminol rearrangement. The synthesis of the proposed inhibitor features an asymmetric intramolecular Mannich reaction, utilizing a chiral sulfinamide. This study presents a novel approach toward the synthesis of functionalized bicyclo[3.1.1]heptanes and highlights an underutilized method to access enantiopure exocyclic amines.

中文翻译：

通过不对称分子内曼尼希反应合成(2R,4S)-4-氨基-5-羟基双环[3.1.1]庚烷-2-甲酸

抑制人鸟氨酸转氨酶会干扰肝细胞癌中的谷氨酰胺和脯氨酸代谢，剥夺肿瘤的必需营养物质。本文报道了一种含有双环[3.1.1]庚醇弹头的基于机制的抑制剂。所提出的失活机制涉及一种新的α-亚胺醇重排。所提出的抑制剂的合成特点是利用手性亚磺酰胺进行不对称分子内曼尼希反应。这项研究提出了一种合成官能化双环[3.1.1]庚烷的新方法，并强调了一种未充分利用的获取对映体纯环外胺的方法。

更新日期：2024-06-10

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