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

Yumeng Lv; Yueshen Feng; Jiatong Dai; Yuying Zhang; Huaxuan Zhang; Zhigang Liu; Huaiji Zheng

doi:10.1021/acs.orglett.2c00797

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

Org Lett. 2022 Apr 15;24(14):2694-2698. doi: 10.1021/acs.orglett.2c00797. Epub 2022 Apr 1.

Authors

Yumeng Lv¹, Yueshen Feng¹, Jiatong Dai¹, Yuying Zhang¹, Huaxuan Zhang¹, Zhigang Liu¹, Huaiji Zheng¹

Affiliation

¹ 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.

PMID: 35362979
DOI: 10.1021/acs.orglett.2c00797

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cyclization
Oxidation-Reduction
Oxidative Stress
Polycyclic Compounds*

Substances

Polycyclic Compounds
calyciphylline N