Total synthesis and stereochemical revision of phacelocarpus 2-pyrone A

Ronson, Thomas O., Burns, Michael J., Voelkel, Martin H. H., Evans, Kieren J. ORCID: https://orcid.org/0000-0003-0111-1709, 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:	Schools > Chemistry Research Institutes & Centres > Cardiff Catalysis Institute (CCI)
Publisher:	Wiley
ISSN:	0947-6539
Last Modified:	06 May 2023 01:57
URI:	https://orca.cardiff.ac.uk/id/eprint/145502

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