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Total synthesis of rupestine G and its epimers.

ABSTRACT: 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 1H ,13C NMR, HRMS, optical rotation value, and experimental and calculated electronic circular dichroism spectroscopy.

SUBMITTER: Yusuf A

PROVIDER: S-EPMC5882726 | biostudies-literature | 2018 Mar

REPOSITORIES: biostudies-literature

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Total synthesis of rupestine G and its epimers.

Yusuf Abdullah A Zhao Jiangyu J Wang Bianlin B Aibibula Paruke P Aisa Haji Akber HA Huang Guozheng G

Royal Society open science 20180328 3

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</ ...[more]

PMID: 29657802

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