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Total synthesis and stereochemical revision of phacelocarpus 2-pyrone A

Ronson, Thomas O., Burns, Michael J., Voelkel, Martin H. H., Evans, Kieren J. ORCID:, Lynam, Jason M., Taylor, Richard J. K. and Fairlamb, Ian J. S. 2015. Total synthesis and stereochemical revision of phacelocarpus 2-pyrone A. Chemistry - A European Journal 21 (52) , pp. 18905-18909. 10.1002/chem.201504089

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The first total synthesis of phacelocarpus 2-pyrone A is reported. The original natural compound was tentatively assigned (by NMR spectroscopy) as containing two cis-alkenes and a trans-vinyl ether connected to a 2-pyrone ring motif. Our computational predictions indicated that a cis-vinyl ether motif was equally feasible. Attempts to prepare the trans-vinyl ether were met with no success. The all cis-target compound was synthesised in nine steps, employing key regio- and stereoselective reactions including AuI-catalysed vinyl etherification, Wittig alkenylation and end-game Stille macrocyclisation. Analysis of the NMR data enabled identification and confirmation of the correct structure of phacelocarpus 2-pyrone A, containing a cis-vinyl ether. Our studies pave the way for future development of methodologies to these structurally distinct pyrone skipped-polyenyne natural products.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Cardiff Catalysis Institute (CCI)
Publisher: Wiley
ISSN: 0947-6539
Last Modified: 10 Nov 2022 10:02

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