Journal article

A serendipitous synthesis of the novel spiroacetal core of cynandione B

Leonie M Tewierik, Christopher D Donner, Jonathan M White, Melvyn Gill

Australian Journal of Chemistry | CSIRO PUBLISHING | Published : 2007


The novel spiroacetal core of cynandione B 2 is prepared from the isochromenone (S)-mellein 4 by treatment with methylmagnesium bromide. The expected lactol product undergoes spontaneous dimerization to form the spiroacetal system 8 as a single diastereoisomer, the stereochemistry of which is established from a single crystal X-ray structure analysis of a methanol solvate. © CSIRO 2007.

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