Stereoselective synthesis of linear oxa-triquinanes and oxa-diquinanes via Lewis acid mediated nucleophilic addition to oxonium ions: study of nucleophile-dependent selectivity

被引：0

作者：

Gharpure, Santosh J. ^{[1
]}

Niranjana, P. ^{[2
]}

Porwal, Suheel K. ^{[3
]}

机构：

[1] Indian Inst Technol, Dept Chem, Mumbai 400076, India

[2] Indian Inst Technol Madras, Dept Chem, Chennai 600036, India

[3] DIT Univ, Dept Chem, Analyt Chem Lab, Dehra Dun 248009, India

来源：

ARKIVOC | 2022年

关键词：

Dioxatriquinanes; oxadiquinanes; polycycles; nucleophiles; ozonolysis; Lewis acids; CLOSING METATHESIS APPROACH; AZA-ANGULAR TRIQUINANES; RADICAL CYCLIZATION; NATURAL-PRODUCTS; CYCLOADDITION; TANDEM; PHOTOREACTIONS; CONSTRUCTION; ACCESS; SERIES;

D O I：

10.24820/ark.5550190.p011.863

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and reliable approach was developed for the stereoselective construction of symmetrical linear dioxatriquinanes and oxadiquinanes via Lewis acid mediated nucleophilic addition to oxonium ion intermediate for etherification of dimethyl acetals. The precursors of linear triquinanes are obtained from the Diels-Alder adducts via ozonolysis in MeOH followed by reductive work-up and subsequent treatment with catalytic H2SO4 to furnish the dimethyl acetal. Further, the stereochemistry of synthesized oxa-bowls was unambiguously established by single crystal X-ray diffraction studies on its derivative.

引用

页码：220 / 238

页数：19

共 2 条

[1] Synthesis of annulated oxa-triquinanes and oxa-diquinanes via cascade Michael addition-intramolecular alkylation involving α-halodicyclopentadienones
Lal, Sohan
Chowdhury, Arindrajit
Namboothiri, Irishi N. N.
TETRAHEDRON, 2017, 73 (10) : 1297 - 1305
[2] Stereoselective Synthesis of Oxa-Bowls by Nucleophilic Addition to Oxonium Ions: Observation of Nucleophile-Dependent Hydride Migration
Gharpure, Santosh J.
Porwal, Suheel K.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (32) : 7277 - 7281

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