Total synthesis of (±)-epi-stemodan-13α,17-diol

Song Chen; Ting Chen; Guanggen Liu; Xiao Wang; Guili Zhu; Yongjiang Liu; Shaomin Fu; Bo Liu

doi:10.1039/C9OB00661C

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Total synthesis of (±)-epi-stemodan-13α,17-diol†

Song Chen,^a Ting Chen,^a Guanggen Liu,^a Xiao Wang,^a Guili Zhu,^a Yongjiang Liu,^a Shaomin Fu*^a and Bo Liu

*^a

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* Corresponding authors

^a Key Laboratory of Green Chemistry &Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China
E-mail: chembliu@scu.edu.cn, fsm09@aliyun.com
Web: http://chem.scu.edu.cn/liubo/
Fax: +86 28 85413712
Tel: +86 28 85413712

Abstract

Stemodan-13α,17-diol is a natural stemodane-type diterpenoid isolated from Stemodia chilensis. Herein we report the total synthesis of its epimer, stemodan-13β,17-diol, by applying titanium-mediated polyene cyclization and iron-catalyzed [5 + 2] cycloaddition as the key transformations to expeditiously install the molecular scaffold.

This article is part of the themed collection: Total synthesis in OBC

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DOI: https://doi.org/10.1039/C9OB00661C
Article type: Communication
Submitted: 21 Mrt. 2019
Accepted: 17 Apr. 2019
First published: 18 Apr. 2019

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Org. Biomol. Chem., 2019,17, 4711-4714

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Total synthesis of (±)-epi-stemodan-13α,17-diol

S. Chen, T. Chen, G. Liu, X. Wang, G. Zhu, Y. Liu, S. Fu and B. Liu, Org. Biomol. Chem., 2019, 17, 4711 DOI: 10.1039/C9OB00661C

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Organic & Biomolecular Chemistry

Total synthesis of (±)-epi-stemodan-13α,17-diol†

Abstract

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Total synthesis of (±)-epi-stemodan-13α,17-diol

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