Issue 1, 2010
From the journal:

Organic & Biomolecular Chemistry

Oxidative spirocyclisation routes towards the sawaranospirolides. Synthesis of ent-sawaranospirolides C and D†

Jeremy Robertson,*a   Praful T. Chovatia,a   Thomas G. Fowler,a   Jonathan M. Witheya  and  Daniel J. Woollastona  

* Corresponding authors

a Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, UK
E-mail: jeremy.robertson@chem.ox.ac.uk
Fax: 44 1865 285002
Tel: 44 1865 275660

Abstract

Two routes are described for the synthesis of the sawaranospirolides, stereoisomeric spirolactone ascorbigenins isolated from Chamaecyparis pisifera. Trapping of the keto enal formed by oxidation of a functionalised 2-(4-hydroxybutyl)furan affords a potential butenolide spiroacetal precursor to sawaranospirolides A and C. Alternatively, epoxidation of protected 3-(dihydropyran-2-yl)-3-arylpropanoic acids results in spirolactonisation to generate ent-sawaranospirolide C; a related acid-mediated spirocyclisation gave access to ent-sawaranospirolide D.

Graphical abstract: Oxidative spirocyclisation routes towards the sawaranospirolides. Synthesis of ent-sawaranospirolides C and D

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Article information

DOI
https://doi.org/10.1039/B918091E
Article type
Paper
Submitted
03 Sep 2009
Accepted
07 Oct 2009
First published
04 Nov 2009

Org. Biomol. Chem., 2010,8, 226-233

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Oxidative spirocyclisation routes towards the sawaranospirolides. Synthesis of ent-sawaranospirolides C and D

J. Robertson, P. T. Chovatia, T. G. Fowler, J. M. Withey and D. J. Woollaston, Org. Biomol. Chem., 2010, 8, 226 DOI: 10.1039/B918091E

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