Total Synthesis and Stereochemical Assignment of (-)-Psychotridine

被引：0
|
作者：
Scott, Tony Z. [1 ]
Armelin, Vinicius F. [1 ]
Movassaghi, Mohammad [1 ]
机构：
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
来源：
ORGANIC LETTERS | 2022年 / 24卷 / 11期
关键词：
ENANTIOSELECTIVE TOTAL-SYNTHESIS; CYCLOTRYPTAMINE ALKALOIDS; PSYCHOTRIA-FORSTERIANA; HODGKINSINE; CONVERGENT;
D O I：
10.1021/acs.orglett.2c00448
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We report the first enantioselective total synthesis and stereochemical assignment of (-)-psychotridine. The application of our diazene-directed assembly of enantiomerically enriched cyclotryptamines afforded a highly convergent synthesis of the pentameric alkaloid, allowing its detailed structural assignment. Highlights of the synthesis include the introduction of four quaternary stereocenters with complete stereochemical control in a single step via the photoextrusion of three molecules of dinitrogen from an advanced intermediate and metal-catalyzed C-H amination reactions in challenging settings.
引用
收藏
页码：2160 / 2164
页数：5
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