A Domino Dearomative ipso-Annulation/Desymmetrization Approach: Stereoselective Access to Tricyclic Alkaloid Skeletons

被引：6
|
作者：
Reddy, Chada Raji [1 ,2 ]
Prasad, Aratikumari Suresh [1 ,2 ]
Ajaykumar, Uprety [1 ,2 ]
机构：
[1] CSIR Indian Inst Chem Technol, Dept Organ Synth & Proc Chem, Hyderabad 500007, Telangana, India
[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, Uttar Pradesh, India
来源：
ORGANIC LETTERS | 2024年 / 26卷 / 23期
关键词：
ENANTIOSELECTIVE DESYMMETRIZATION; QUATERNARY STEREOCENTERS; STEREOGENIC CENTERS; N-BENZYLACRYLAMIDES; SPIROCYCLIZATION; CYCLIZATION; CYCLOHEXADIENONES; CONSTRUCTION;
D O I：
10.1021/acs.orglett.4c01407
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Herein, we reveal an unprecedented domino annulation of N-benzyl-acrylamides with 1,3-dicarbonyls for the assembly of fused tricyclic alkaloid frameworks incorporating a spirocycle via an alkylation/dearomative ipso-annulation/Michael addition (desymmetrization) sequence. This conversion involves three carbon-carbon bond formations, generating four chiral carbons, including three quaternary carbon centers, in a single diastereomer in one pot under identical reaction conditions. The synthetic potential of this atom-economic method is illustrated by modifications of the functional groups present in the products obtained.
引用
收藏
页码：4904 / 4909
页数：6
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