Synthesis of the 1, 3-dioxolane ring system of the trichothecenes sambucinol and sporol via a stereoselective Claisen rearrangement

FE Ziegler, A Nangia, G Schulte

Index: Ziegler,F.E.; Nangia,A.; Schulte,G. Journal of the American Chemical Society, 1987 , vol. 109, p. 3987

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Citation Number: 20

Abstract

Abstract: The major stereoisomer from the Claisen rearrangement of allyl vinyl ether 10 was shown to be keto nitrile 12 by an X-ray crystallographic analysis on the derived hydroxy nitrile 15. In a similar fashion, allyl vinyl ether 22 produced keto nitrile 23a. This substance was converted into hydroxymethyl ketal 25, which bears the 1, 3-dioxolane ring system present in sambucinol 1 and sporol 2.