Issue 15, 2013
From the journal:

Organic & Biomolecular Chemistry

Asymmetric synthesis of cyclo-archaeol and β-glucosyl cyclo-archaeol†

Catalina Ferrer,a   Peter Fodran,a   Santiago Barroso,a   Robert Gibson,b   Ellen C. Hopmans,b   Jaap Sinninghe Damsté,b   Stefan Schouten*b  and  Adriaan J. Minnaard*a  

* Corresponding authors

a Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG Groningen, The Netherlands
E-mail: A.J.Minnaard@rug.nl
Tel: +31 50 3634235

b NIOZ Royal Netherlands Institute for Sea Research, Department of Marine Organic Biogeochemistry, P.O. Box 59, 1790 AB Den Burg, The Netherlands
E-mail: Stefan.Schouten@nioz.nl

Abstract

An efficient asymmetric synthesis of cyclo-archaeol and β-glucosyl cyclo-archaeol is presented employing catalytic asymmetric conjugate addition and catalytic epoxide ring opening as the key steps. Their occurrence in deep sea hydrothermal vents has been confirmed by chromatographic comparison with natural samples.

Graphical abstract: Asymmetric synthesis of cyclo-archaeol and β-glucosyl cyclo-archaeol

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Article information

DOI
https://doi.org/10.1039/C3OB27277J
Article type
Paper
Submitted
23 Nov 2012
Accepted
12 Feb 2013
First published
12 Feb 2013

Org. Biomol. Chem., 2013,11, 2482-2492

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Asymmetric synthesis of cyclo-archaeol and β-glucosyl cyclo-archaeol

C. Ferrer, P. Fodran, S. Barroso, R. Gibson, E. C. Hopmans, J. S. Damsté, S. Schouten and A. J. Minnaard, Org. Biomol. Chem., 2013, 11, 2482 DOI: 10.1039/C3OB27277J

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