Total synthesis of rupestine G and its epimers | Zendy

Abdulla Yusuf | Zendy; Jiangyu Zhao | Zendy; Bianlin Wang | Zendy; Paruke Aibibula | Zendy; Haji Akber Aisa | Zendy; Guozheng Huang | Zendy

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Total synthesis of rupestine G and its epimers

Author(s) -

Abdulla Yusuf,

Jiangyu 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.

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