Synthesis of the [6.6.7.5] Tetracyclic Core of Calyciphylline N via a Boc-Mediated Oxidative Dearomatization/Diels–Alder Approach

Synthesis of the [6.6.7.5] Tetracyclic Core of Calyciphylline N via a Boc-Mediated Oxidative Dearomatization/Diels–Alder Approach

A sequential process involving Boc-mediated oxidative dearomatization and inter/intramolecular Diels–Alder reaction was investigated. Based on an intermolecular Diels–Alder reaction and subsequently a radical 7-endo-trig type cyclization, the [6.6.7.5] tetracyclic core of Calyciphylline N was assemb...

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Bibliographic Details
Published in:Organic letters Vol. 24; no. 14; pp. 2694 - 2698
Main Authors: Lv, Yumeng, Feng, Yueshen, Dai, Jiatong, Zhang, Yuying, Zhang, Huaxuan, Liu, Zhigang, Zheng, Huaiji
Format: Journal Article
Language:English
Published: United States American Chemical Society 15-04-2022
Subjects:
Cyclization
Oxidation-Reduction
Oxidative Stress
Polycyclic Compounds
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Summary:A sequential process involving Boc-mediated oxidative dearomatization and inter/intramolecular Diels–Alder reaction was investigated. Based on an intermolecular Diels–Alder reaction and subsequently a radical 7-endo-trig type cyclization, the [6.6.7.5] tetracyclic core of Calyciphylline N was assembled.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c00797