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Synlett 1999; 1999(9): 1359-1362
DOI: 10.1055/s-1999-2851
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Singlet Oxygen Cycloaddition to Dienes: a Biomimetic Approach to Marine Endoperoxides?

L. M. Harwood* , J. Robertson, S. Swallow
  • *Department of Chemistry, University of Reading, Whiteknights, Reading RG6 6AD, UK; Fax + 44(0)11 89 31 67 82; E-mail: l.m.harwood@reading.ac.uk
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Publication Date:
31 December 1999 (online)

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Singlet oxygen addition studies to a series of diene substrates indicate that trisubstituted dienes undergo ene reaction selectively, indicating that the biosynthetic construction of the mycaperoxides, norsesterterpenes isolated from sponges of the genus Mycale, containing a trisubstituted endoperoxide subunit, probably does not proceed via a 4 + 2 singlet oxygen cycloaddition pathway.

singlet oxygen - ene reaction - 4 + 2 cycloaddition - mycaperoxide - marine endoperoxide