Prins cyclization of 1,3-dioxinone: synthesis of 11-epi-badkhysin

By:Xu, Xiaoliang ; Hua, Ping;Xu, Yiren ; He, Baoqing ; Zhao, Jingfeng;Li, Liang ; Chen, Wen  ; Zhang, Hongbin

Organic Chemistry Frontiers

DOI：https://doi.org/10.1039/d4qo00162a

Published：2024-04-16

Abstract

The asymmetric synthesis of highly functional 11-epi-badkhysin has been accomplished using a structure-unit based approach. Key reactions of the synthesis are a ketone-participated Prins cyclization of 1,3-dioxinone to install the decahydro-4,8-epoxyazulene scaffold, a BBr3-promoted homoallylenol formation to prepare the common intermediate for sesquiterpenoids, and an alkylation/reduction/lactonization sequence to construct the core 5-7-5 tricyclic ring system bearing the cis-annulated gamma-butyrolactone moiety.