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Synthesis 2002(14): 2150-2154
DOI: 10.1055/s-2002-34370
DOI: 10.1055/s-2002-34370
PAPER
© Georg Thieme Verlag Stuttgart · New York
Mechanistic Observations on the Unusual Reactivity of Dioxenone Photosubstrates in the Synthesis of Ingenol
Further Information
Received
14 August 2002
Publication Date:
26 September 2002 (online)
Publication History
Publication Date:
26 September 2002 (online)
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Abstract
The irradiation of allylically substituted dioxenone photosubstrates 6 and 21 lead to unexpected products, the formation of which can be explained by a series of transannular hydrogen atom abstractions.
Key Words
photochemistry - natural products - rearrangements - radicals - cycloadditions
- 3
Winkler J.Henegar K.Rouse M.Greaney M.Harrison S.Jeon Y. J. Am. Chem. Soc. 2002, 124: 9726 - 4
Winkler J.Henegar K.Williard P. J. Am. Chem. Soc. 1987, 109: 2850 - 5
Winkler J.Shao B. Tetrahedron Lett. 1993, 34: 3355 - 6
Tan EW.Chan B.Blackman A. J. Am. Chem. Soc. 2002, 124: 2078
References
Current address: Millennium Pharmaceuticals, Cambridge, MA, USA.
2Current address: Department of Chemistry, University of Edinburgh, UK.