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Synthesis of (±)-solanapyrones A and B

✍ Scribed by Barry Lygo; Mohamed Bhatia; Jason W.B. Cooke; David J. Hirst

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
293 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

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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Synthesis of (±)-solanapyrone A
Synthesis of (±)-solanapyrone A
✍ Akitami Ichihara; Masayoshi Miki; Hiroyuki Tazaki; Sadao Sakamura 📂 Article 📅 1987 🏛 Elsevier Science 🌐 French ⚖ 209 KB

The first synthesis of solanapyrone A m, a phytotoxin from Alternaria solani, has been completed through the intramolecular Diels-Alder reaction. Solanapyrone A (1) is a principal phytotoxin recently isolated along with other metabolites, solanapyxnes B &, C k)' and zinnolide', from the culture brot