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

页码：3034 / 3039

页数：6

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