A serendipitous synthesis of the novel spiroacetal core of cynandione B

Abstract

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.