Issue 15, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Acid catalysed rearrangement of a spiroketalenol ether. An easy synthesis of chrycorin

Biao-Lin Yin,a   Yikang Wua  and  Yu-Lin Wu*a  

* Corresponding authors

a State Key Laboratory of Bio-organic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China
E-mail: ylwu@pub.sioc.ac.cn

Abstract

Tonghaosu, 2-[(Z)-hexa-2,4-diynylidene]-1,6-dioxaspiro[4,4]non-3-ene (1a), and its spiroketal enol ether analogues (1b–d and 2) were efficiently converted into interesting cyclopentenone derived oxabicyclic compounds. By applying this reaction protocol the natural product chrycorin was easily synthesized in its racemic form. A reaction mechanism for this is proposed.

Graphical abstract: Acid catalysed rearrangement of a spiroketal enol ether. An easy synthesis of chrycorin

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Article information

DOI
https://doi.org/10.1039/B205229F
Article type
Communication
Submitted
29 May 2002
Accepted
26 Jun 2002
First published
05 Jul 2002

J. Chem. Soc., Perkin Trans. 1, 2002, 1746-1747

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Acid catalysed rearrangement of a spiroketal enol ether. An easy synthesis of chrycorin

B. Yin, Y. Wu and Y. Wu, J. Chem. Soc., Perkin Trans. 1, 2002, 1746 DOI: 10.1039/B205229F

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