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

Org Lett

Shaanxi Key Laboratory of Natural Products and Chemical Biology, College of Chemistry and Pharmacy, Northwest Agriculture and Forestry University, 3 Taicheng Road, Yangling 712100, China.

Published: April 2022

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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http://dx.doi.org/10.1021/acs.orglett.2c00797DOI Listing

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