Enantioselective Synthesis of Isocarbostyril Alkaloids and Analogs Using Catalytic Dearomative Functionalization of Benzene

被引：61

作者：

Bingham, Tanner W. ^{[1
]}

Hernandez, Lucas W. ^{[1
]}

Olson, Daniel G. ^{[1
]}

Svec, Riley L. ^{[1
]}

Hergenrother, Paul J. ^{[1
]}

Sarlah, David ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2019年 / 141卷 / 01期

关键词：

ASYMMETRIC TOTAL-SYNTHESIS; ANTINEOPLASTIC AGENTS; AMARYLLIDACEAE ISOCARBOSTYRILS; N-METHYLTRIAZOLINEDIONE; NARCICLASINE ALKALOIDS; ENT-LYCORICIDINE; (+)-PANCRATISTATIN; (+)-LYCORICIDINE; PANCRATISTATIN; ANTITUMOR;

D O I：

10.1021/jacs.8b12123

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Enantioselective total syntheses of the anticancer isocarbostyril alkaloids (+)-7-deoxypancratistatin, (+)-pancratistatin, (+)-lycoricidine, and (+)-narciclasine are described. Our strategy for accessing this unique class of natural products is based on the development of a Nicatalyzed dearomative trans-1,2-carboamination of benzene. The effectiveness of this dearomatization approach is notable, as only two additional olefin functionalizations are needed to construct the fully decorated aminocyclitol cores of these alkaloids. Installation of the lactam ring has been achieved through several pathways and a direct interconversion between natural products was established via a late-stage C-7 cupration. Using this synthetic blueprint, we were able to produce natural products on a gram scale and provide tailored analogs with improved activity, solubility, and metabolic stability.

引用

页码：657 / 670

页数：14

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