Total synthesis of (−)-8-epi-chromazonarol enabled by a unique N2H4·H2O promoted intramolecular oxa-Michael cyclization reaction

Lin Liu; Huayue Song; Peng Chen; Ziyun Yuan; Shangbiao Feng; Weiwei Zhang; Bowen Fang; Xingang Xie; Xuegong She

doi:10.1039/C8QO00901E

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Total synthesis of (−)-8-epi-chromazonarol enabled by a unique N₂H₄·H₂O promoted intramolecular oxa-Michael cyclization reaction†

Lin Liu,‡^a Huayue Song,‡^a Peng Chen,^a Ziyun Yuan,^a Shangbiao Feng,^a Weiwei Zhang,^a Bowen Fang,^b Xingang Xie

*^a and Xuegong She

Author affiliations

* Corresponding authors

^a State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 South Tianshui Road, Lanzhou, P. R. China
E-mail: xiexg@lzu.edu.cn

^b Chemical Engineering Institute, Northwest University for Nationalities, Lanzhou, People's Republic of China

Abstract

An enantioselective total synthesis of the natural chroman-sesquiterpenoid (−)-8-epi-chromazonarol has been accomplished by a unique N₂H₄·H₂O promoted highly diastereo-selective oxa-Michael cyclization to construct the central chroman framework and assemble the unusual C8 stereocenter. The other salient feature of the reported synthesis involves a Stille carbonylative cross-coupling reaction to link the aryl stannane 9 and bicyclic triflate 10.

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Article information

DOI: https://doi.org/10.1039/C8QO00901E
Article type: Research Article
Submitted: 21 Aug 2018
Accepted: 15 Sep 2018
First published: 17 Sep 2018

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Org. Chem. Front., 2018,5, 3013-3017

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Total synthesis of (−)-8-epi-chromazonarol enabled by a unique N₂H₄·H₂O promoted intramolecular oxa-Michael cyclization reaction

L. Liu, H. Song, P. Chen, Z. Yuan, S. Feng, W. Zhang, B. Fang, X. Xie and X. She, Org. Chem. Front., 2018, 5, 3013 DOI: 10.1039/C8QO00901E

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