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Synlett 2014; 25(17): 2471-2474
DOI: 10.1055/s-0034-1379001
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© Georg Thieme Verlag Stuttgart · New York

Synthetic Studies toward Lindenane-Type Sesquiterpenoid Dimers

Li Yang
a   Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. of China   Fax: +86(28)85413712   Email: chembliu@scu.edu.cn
,
Guizhou Yue
a   Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. of China   Fax: +86(28)85413712   Email: chembliu@scu.edu.cn
,
Changchun Yuan
a   Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. of China   Fax: +86(28)85413712   Email: chembliu@scu.edu.cn
,
Biao Du
a   Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. of China   Fax: +86(28)85413712   Email: chembliu@scu.edu.cn
,
Heping Deng
a   Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. of China   Fax: +86(28)85413712   Email: chembliu@scu.edu.cn
,
Bo Liu*
a   Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. of China   Fax: +86(28)85413712   Email: chembliu@scu.edu.cn
b   State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing 210009, P. R. of China
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Publication History

Received: 14 June 2014

Accepted after revision: 26 July 2014

Publication Date:
25 August 2014 (online)

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Abstract

The key transformation for the total synthesis of the lindenane sesquiterpenoid dimers is the intermolecular Diels–Alder reaction between two lindenane-type monomers. Herein we report our efforts made on examination of the biogenetic hypothesis and the inverse-electron-demand Diels–Alder (IEDDA) reaction. The combination of Tf2NH/AlMe3 was developed to catalyze the model IEDDA reaction.

Key words

sesquiterpene - dimer - Diels–Alder cycloaddition - total synthesis - biomimetic

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    for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000083.
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