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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., 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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Abstract

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: 17 Dec 2021 15:30
URI: https://orca.cardiff.ac.uk/id/eprint/145502

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