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Synthesis of (±)-solanapyrones A and B |
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| Authors: | Barry LygoJason W.B. Cooke David J. Hirst |
| Affiliation: | a School of Chemistry, University of Nottingham, Nottingham NG7 2RD, UK b Department of Chemistry, University of Salford, Salford M5 4WT, UK c GlaxoSmithKline, Gunnels Wood Road, Stevenage, Herts SG1 2NY, UK |
| Abstract: | In this paper we report the development of a stereoselective IMDA approach to the phytotoxic polyketides (±)-solanapyrones A and B. The stereoselectivity of the key IMDA cycloaddition was optimized by investigating a range of 2,8,10-dodecatrienoic acid derivatives. This established that use of the Weinreb amide led to the desired exo-selectivity and also facilitated construction of the pyrone moiety. A novel approach to the installation of the C-3 formyl group in solanapyrone A is also described. |
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