Highly efficient construction of an oxa-[3.2.1]octane-embedded 5-7-6 tricyclic carbon skeleton and ring-opening of the bridged ring via C-O bond cleavage

Yi Cui; Jiayuan Lv; Tianhang Song; Jun Ren; Zhongwen Wang

doi:10.1039/d2ra01315k

Highly efficient construction of an oxa-[3.2.1]octane-embedded 5-7-6 tricyclic carbon skeleton and ring-opening of the bridged ring via C-O bond cleavage

RSC Adv. 2022 Mar 25;12(16):9519-9523. doi: 10.1039/d2ra01315k.

Authors

Yi Cui¹, Jiayuan Lv¹, Tianhang Song¹, Jun Ren¹, Zhongwen Wang¹

Affiliation

¹ State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University Tianjin 300071 PR China wzwrj@nankai.edu.cn.

Abstract

We report herein a highly efficient strategy for construction of a bridged oxa-[3.2.1]octane-embedded 5-7-6 tricyclic carbon skeleton through [3 + 2] IMCC (intramolecular [3 + 2] cross-cycloaddition), and the substituents and/or stereochemistries on C-4, C-6, C-7 and C-10 fully match those in the rhamnofolane, tigliane and daphnane diterpenoids. Furthermore, ring-opening of the bridged oxa-[3.2.1]octane via C-O bond cleavage was also successfully achieved.