Issue 20, 2013
From the journal:

Organic & Biomolecular Chemistry

Diastereoselective synthesis of vicinal cis-dihydroxyheterospirocycles by one-pot epoxidation/spirocyclization of C(3)-functionalized cyclohex-2-en-1-ols†

Ming-Chang P. Yeh,*a   Chia-Jung Liang,a   Cheng-Yuan Liu,a   Ya-fon Shih,a   I-Chen Lee,a   Hsiang-Fang Liua  and  Jeng-Long Wang*b  

* Corresponding authors

a Department of Chemistry, National Taiwan Normal University, Taipei, Taiwan
E-mail: cheyeh@ntnu.edu.tw
Fax: +886 2 29324249
Tel: +886 2 77346119

b Department of Nursing, Meiho University, Neipu, Pintung, Taiwan
E-mail: x00002042@mail.meiho.edu.tw
Fax: +886 8 7797871
Tel: +886 8 7799821, #8192

Abstract

Spirolactones, spirotetrahydrofurans, and spiropyrrolidines containing a vicinal cis-diol adjacent to the spiro-carbon center are prepared by one-pot epoxidation/spirocyclization of cyclohex-2-en-1-ols bearing an ester, alcohol, or amide functional side chain at the C(3) position of the ring.

Graphical abstract: Diastereoselective synthesis of vicinal cis-dihydroxyheterospirocycles by one-pot epoxidation/spirocyclization of C(3)-functionalized cyclohex-2-en-1-ols

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Article information

DOI
https://doi.org/10.1039/C3OB27352K
Article type
Paper
Submitted
04 Dec 2012
Accepted
08 Mar 2013
First published
08 Mar 2013

Org. Biomol. Chem., 2013,11, 3393-3399

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Diastereoselective synthesis of vicinal cis-dihydroxyheterospirocycles by one-pot epoxidation/spirocyclization of C(3)-functionalized cyclohex-2-en-1-ols

M. P. Yeh, C. Liang, C. Liu, Y. Shih, I. Lee, H. Liu and J. Wang, Org. Biomol. Chem., 2013, 11, 3393 DOI: 10.1039/C3OB27352K

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