Diels-Alder/Oxidative Aromatization Approach towards the All-Carbon DEF Tricyclic Skeleton of Daphenylline

• Published in: Chemistry, an Asian journal Vol. 9; no. 5; pp. 1274 - 1277
• Main Authors: Li, Huilin, Qiu, Yangcheng, Zhao, Changgui, Yuan, Ziyun, Xie, Xingang, She, Xuegong
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.05.2014; WILEY‐VCH Verlag; Wiley Subscription Services, Inc
• Subjects: alkaloids; Alkaloids - chemical synthesis; Alkaloids - chemistry; aromatization; Chemistry; Cycloaddition Reaction; daphenylline; Diels-Alder; Molecular Structure; natural products; Oxidation-Reduction; natural products; aromatization; Diels-Alder; daphenylline; alkaloids

Daphenylline is a recently isolated Daphniphyllum alkaloid with an unprecedented novel hexacyclic scaffold. In this study, the synthesis of the fused all‐carbon DEF tricyclic skeleton of daphenylline has been accomplished. Key steps of the reported sequence involve Evans asymmetric allylation, aldol...