A Serendipitous Synthesis of the Novel Spiroacetal Core of Cynandione B

Leonie M. Tewierik; Christopher D. Donner; Jonathan M. White; Melvyn Gill

doi:10.1071/CH06472

RESEARCH ARTICLE

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A Serendipitous Synthesis of the Novel Spiroacetal Core of Cynandione B

Leonie M. Tewierik ^A , Christopher D. Donner ^A ^B ^C , Jonathan M. White ^A ^B and Melvyn Gill ^A ^*

+ Author Affiliations

- Author Affiliations

^A School of Chemistry, University of Melbourne, Melbourne VIC 3010, Australia.

^B Bio21 Molecular Science and Biotechnology Institute, University of Melbourne, Melbourne VIC 3010, Australia.

^C Corresponding author. Email: cdonner@unimelb.edu.au

Australian Journal of Chemistry 60(2) 89-92 https://doi.org/10.1071/CH06472
Submitted: 14 December 2006 Accepted: 10 January 2007 Published: 13 February 2007

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.

Acknowledgments

C.D.D. is grateful for support through the Australian Research Council Centres of Excellence Program; L.M.T. is grateful for a Melbourne Research Scholarship.

References

^* Deceased.

A Serendipitous Synthesis of the Novel Spiroacetal Core of Cynandione B

Abstract

Acknowledgments

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