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

页码：2160 / 2164

页数：5

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