The synthesis of C1-functionalized β-carbolines from N-Boc norharman is described. Substitution is realized by employing the Knochel–Hauser base (TMPMgCl·LiCl) followed by transmetalation with ZnCl₂ and subsequent Negishi cross-coupling of the resulting organozinc species. A variety of aryl or heteroaryl bromides participated in this one-pot reaction sequence, allowing for rapid diversification of the β-carboline scaffold in moderate to excellent yields. The reaction protocol has been applied to the synthesis of natural alkaloids nitramarine, nitraridine, eudistomin U, and perlolyrine.

中文翻译：

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C1 通过 Knochel-Hauser 碱导向金属化和 Negishi 偶联实现 β-Carboline 的功能化


描述了从 N-Boc norharman 合成 C1 官能化 β-咔啉。通过使用 Knochel-Hauser 基 （TMPMgCl·LiCl），然后用 ZnCl₂ 进行金属转移，随后得到的有机锌物质的 Negishi 交叉偶联。多种芳基或杂芳基溴参与了这个单锅法反应序列，从而能够以中等至极高的收率实现 β-咔啉支架的快速多样化。该反应方案已应用于天然生物碱硝草胺、硝糖苷、eudistomin U 和 perlolyrine 的合成。