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Intramolecular competition between the di-π-methane and the oxa-di-π-methane rearrangements in a triplet-excited β, γ, β1, γ1-dienone.

✍ Scribed by Reinout van der Veen; Cornelis Kruk; Hans Cerfontain

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
171 KB
Volume
101
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

The triplet photosensitization of the β, γ, β^1^, γ^1^‐dienone 2 leads to the formation of the DPM isomer 6 and the two ODPM isomers 7 and 8 in a ratio of 35:17:10. This is the first reported example of a substrate which exhibits intramolecular competition as demonstrated by the occurrence of both the DPM and ODPM rearrangement.

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## Abstract The irradiation of 17β‐acetoxy‐4‐oxa‐1,5‐androstadien‐3‐one (**12**) yielded the two stereoisomeric spiro‐lactones **13** and **14**, which result from a di‐π‐methane photorearrangement. A third product, the oxa‐anthrasteroid **15**, was also isolated (__Scheme 3__).