Biomimetic Synthesis of Azorellolide via Cyclopropylcarbinyl Cation Chemistry

被引：2
作者：
Artzy, Jordan Y. [1 ]
Tantillo, Dean J. [2 ]
Trauner, Dirk H. [1 ]
机构：
[1] Univ Penn, Dept Chem, Philadelphia, PA 19104 USA
[2] Univ Calif Davis, Dept Chem, Davis, CA 95616 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2024年 / 147卷 / 01期
基金：
美国国家科学基金会;
关键词：
DENSITY FUNCTIONALS; CARBON SKELETON; BICYCLOBUTONIUM; INTERCONVERSION; BIOSYNTHESIS; INTERMEDIATE; DITERPENES;
D O I：
10.1021/jacs.4c14664
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A concise synthesis of the complex diterpene azorellolide, inspired by speculations on biosynthetic cationic cascades, is presented. The approach, guided by computation, relies on the intramolecular interception of a cyclopropylcarbinyl cation by an appended carboxylate. The successful execution of this strategy was achieved through acid-catalyzed isomerization of a beta-lactone in competition with a type I dyotropic rearrangement.
引用
收藏
页码：78 / 83
页数：6
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