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Synthesis of (±)-solanapyrone A

✍ Scribed by Akitami Ichihara; Masayoshi Miki; Hiroyuki Tazaki; Sadao Sakamura

Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
209 KB
Volume
28
Category
Article
ISSN
0040-4039

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✦ Synopsis

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 broth of Alternaria solani -3 a causal fungus of early blight disease of potato and tomato. l-induced a necrotic lesion on the leaf of potato, and showed Since this toxin has been obtained as an elucidated on the basis of spectroscopic MIC value of 25 -50 ppm to Pyricularia oryzae. oil, the structure and stereochemistry have been data and chemical reactions 133 . In order to confirm

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Synthesis of (±)-solanapyrones A and B
Synthesis of (±)-solanapyrones A and B
✍ Barry Lygo; Mohamed Bhatia; Jason W.B. Cooke; David J. Hirst 📂 Article 📅 2003 🏛 Elsevier Science 🌐 French ⚖ 293 KB

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 W