Stereoselective Desymmetrization of Cyclohexadienone-Tethered Enones: Efficient Access to Highly Strained Polycyclic Indoles

被引：30

作者：

Thopate, Satish B. ^{[1
,3
]}

Jadhav, Sandip B. ^{[1
,3
]}

Nanubolu, Jagadeesh Babu ^{[2
,3
]}

Chegondi, Rambabu ^{[1
,3
]}

机构：

[1] IICT, CSIR, Dept Organ Synth & Proc Chem, Hyderabad 500007, Andhra Pradesh, India

[2] IICT, CSIR, Dept Analyt Chem, Hyderabad 500007, Andhra Pradesh, India

[3] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India

来源：

ACS CATALYSIS | 2019年 / 9卷 / 11期

关键词：

desymmetrization; Friedel-Crafts alkylation; cyclohexadienone; indole alkaloid; cascade annulation; FRIEDEL-CRAFTS ALKYLATION; ONE-POT; ENANTIOSELECTIVE SYNTHESIS; ACTINOPHYLLIC ACID; 4+3 CYCLOADDITION; CYCLIZATION; CASCADE; REARRANGEMENT; CONSTRUCTION; ANNULATION;

D O I：

10.1021/acscatal.9b03560

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A highly regioselective and stereoselective cascade annulation of indoles with C2-symmetric enone tethered-cyclohexadienones provides rapid access to complex indole alkaloid-like scaffolds in high yields. Interestingly, a different reaction course was observed with 3-substituted indoles giving C-2/N annulation products with similar complexity via intramolecular aza-Michael addition. This desymmetrization approach is highly practical and allows atom-economical synthesis of natural product-like molecules containing several contiguous stereocenters with broad range of substrate scope and high functional-group tolerance. The synthetic utility of the products was demonstrated with various chemoselective, regioselective, and diastereoselective transformations on the highly strained polycyclic indoles to elaborate the value of this tandem reaction.

引用

页码：10012 / 10019

页数：15

共 70 条

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