Open AccessTotal synthesis of rupestine G and its epimers
Author(s) -
Abdullah Yusuf,
Jiaheng Zhao,
Bianlin Wang,
Paruke Aibibula,
Haji Akber Aisa,
Guozheng Huang
Publication year - 2018
Publication title -
royal society open science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.84
H-Index - 51
ISSN - 2054-5703
DOI - 10.1098/rsos.172037
Subject(s) - epimer , moiety , circular dichroism , diene , specific rotation , stereochemistry , yield (engineering) , chemistry , total synthesis , nuclear magnetic resonance spectroscopy , optical rotation , organic chemistry , materials science , natural rubber , metallurgy
Rupestine G is a guaipyridine sesquiterpene alkaloid isolated from Artemisia rupestris L. The total synthesis of rupestine G 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 G and its three epimers were obtained as a mixture in a sequence of nine linear steps with 18.9% yield. Rupestine G and its optically pure isomers were isolated by chiral preparative HPLC and fully characterized by 1 H , 13 C NMR, HRMS, optical rotation value, and experimental and calculated electronic circular dichroism spectroscopy.