Total Synthesis of Rupestine G and Its Epimers

Overview

Journal R Soc Open Sci

Specialty Science

Date 2018 Apr 17

PMID 29657802

Citations 1

Authors

Abdullah Yusuf

Jiangyu Zhao

Bianlin Wang

Paruke Aibibula

Haji Akber Aisa

Guozheng Huang

Affiliations

Soon will be listed here.

Abstract

Rupestine is a guaipyridine sesquiterpene alkaloid isolated from L. The total synthesis of rupestine and its epimers was accomplished employing a Suzuki reaction to build a terminal diene moiety. The diene was further elaborated into the desired guaipyridine structure by a ring-closing metathesis reaction. Over all, rupestine and its three epimers were obtained as a mixture in a sequence of nine linear steps with 18.9% yield. Rupestine and its optically pure isomers were isolated by chiral preparative HPLC and fully characterized by H ,C NMR, HRMS, optical rotation value, and experimental and calculated electronic circular dichroism spectroscopy.

Citing Articles

Synthesis of Guaipyridine Alkaloids Rupestine M and L by Cycloaddition/Cycloreversion of an Intermediate 1,4-Oxazinone.

Scheerer J, Leeth E, Sprow J Synthesis (Stuttg). 2023; 55(15):2319-2324.

PMID: 37691879 PMC: 10489027. DOI: 10.1055/s-0042-1751413.

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