Catalyst-Controlled Diastereoselective Synthesis of Bridged [3.3.1] Bis(Indolyl)-Oxanes and Oxepanes via Desymmetrization of Bis(Indolyl)-Cyclohexadienones

被引：3
|
作者：
Mishra, Abhishek Kumar [1 ]
Chauhan, Anil [1 ,2 ]
Kumar, Santosh [1 ,2 ]
Kant, Ruchir [3 ]
Kumar, Ravindra [1 ,2 ]
机构：
[1] CSIR Cent Drug Res Inst, Div Med & Proc Chem, Lucknow 226031, Uttar Pradesh, India
[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, Uttar Pradesh, India
[3] CSIR Cent Drug Res Inst, Mol & Struct Biol Div, Lucknow 226031, Uttar Pradesh, India
来源：
ORGANIC LETTERS | 2023年 / 25卷 / 17期
关键词：
ASYMMETRIC TRANSFORMATIONS; INDOLE ALKALOIDS; MARINE SPONGE; CYCLIZATION; FUNCTIONALIZATION; ANTIFUNGAL; 1,6-ENYNES; ANALOGS; ALKYNE;
D O I：
10.1021/acs.orglett.3c00834
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A catalyst-controlled divergent synthesis of bridged [3.3.1] bis(indolyl)-oxanes and cis-[6.7] fused bis(indolyl) oxepanes via diastereoselective desymmetrization of bis(indolyl)-cyclohexadienones is presented for the first time. The reaction is highly atom-and step-economic, furnishing sp3-rich functionalized bis(indolyl) derivatives in good to excellent yields with wide substrate scope. The reaction proceeds through Friedel-Crafts alkylation followed by catalyst-controlled selective C-C bond formation/rearrangement. Gram scale synthesis and synthetic utility to generate bis(indolyl) alkaloid-like molecular diversity were also illustrated.
引用
收藏
页码：3034 / 3039
页数：6
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