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A Model Study of the Mechanism of the Type B (Di-π-methane) and Lumiketone Rearrangement in Rotationally Constrained α,β-Enones

✍ Scribed by Reguero, Mar; Bernardi, Fernando; Olivucci, Massimo; Robb, Michael A.

Book ID
126116684
Publisher
American Chemical Society
Year
1997
Tongue
English
Weight
232 KB
Volume
62
Category
Article
ISSN
0022-3263

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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__).