In studies directed towards the synthesis of 25-hydroxybrassinolide 1 we found, that upon reaction of intermediate 7 with trimethylaluminium–n-butyllithium an alkylating fission of the epoxide ring and rearrangement of the tetrahydropyranyl unit takes place to afford after deprotection the new dioxonane-annelated brassinosteroid 9.
D. Lichtblau, A. Porzel, J. Schmidt, B. Voigt and G. Adam, J. Chem. Soc., Perkin Trans. 1, 1999, 53 DOI: 10.1039/A807078D
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