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

Jeremy Robertson; Praful T. Chovatia; Thomas G. Fowler; Jonathan M. Withey; Daniel J. Woollaston

doi:10.1039/B918091E

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Organic & Biomolecular Chemistry

Issue 1, 2010

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

Jeremy Robertson , Praful T. Chovatia , Thomas G. Fowler , Jonathan M. Withey and Daniel J. Woollaston

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

DOI: 10.1039/B918091E
Received 03 Sep 2009, Accepted 07 Oct 2009
First published on the web 04 Nov 2009

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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.

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Experimental details for Schemes 3, 4 and 6; copies ofselected ¹H and ¹³C NMR spectra for the compounds in Schemes 7 and8
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Jeremy Robertson
Praful T. Chovatia
Thomas G. Fowler
Jonathan M. Withey
Daniel J. Woollaston

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Organic & Biomolecular Chemistry

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

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