Alkylation studies on Hagemann's ester: an approach to the synthesis of the trisporic acids Public Deposited

http://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/6q182p86x

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  • Sequential alkylation of Hagemann's ester with methyl and methallyl halides has been studied. Treatment of Hagemann's ester with methyl iodide and sodium ethoxide gave a mixture of 21 and 25 in a ratio of 4:1. Alkylation of 21 with methallyl chloride and potassium t-butoxide afforded a mixture of 37 and 38 in a ratio of 2:1. Keto ester 37 reacted with methyl iodide to furnish 47, which underwent Cope rearrangement to give 33. Oxidative cleavage of the terminal C=C of 33 with osmium tetroxide and sodium periodate afforded diketo ester 48.
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