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Synthesis, structure, and reactivity of secosteroids containing a medium-sized ring. Part 32. Conformations and photochemical reactivity of some unsaturated 5,10-secosteroidal ketones

✍ Scribed by Ljubinka Lorenc; Vladimir Pavlović; Mihailo Lj. Mihailović; Jaroslav Kalvoda; Hermann Fuhrer

Publisher
John Wiley and Sons
Year
1991
Tongue
German
Weight
283 KB
Volume
74
Category
Article
ISSN
0018-019X

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✦ Synopsis

Dedicated to Professor Kurt Schaffner on the occasion of his 60th birthday (12.VIII. 91) UV irradiation of the unsaturated (E)-S,lO-secosteroidal ketones 1 and 6 results, in addition to (E/Z)-isomerization, in an intramolecular Paterno-Biichi reaction and, in the case of 1, in transannular cyclization (along with AcOH elimination). The stereochemistry of the observed intramolecular photoprocesses can be explained in terms of ground-state conformations of the (E)-seco-ketones 1 and 6 in solution.

📜 SIMILAR VOLUMES

Synthesis, Structure, and Reactivity of
Synthesis, Structure, and Reactivity of Secosteroids Containing a Medium-Sized Ring. Part 36. Transannular photocyclization of some unsaturated 5,10-secosteroidal ketones: A reevaluation
✍ Roland Heckendorn; Hermann Fuhrer; Jaroslav Kalvoda; Ljubinka Lorenc; Vladimir P 📂 Article 📅 1995 🏛 John Wiley and Sons 🌐 German ⚖ 311 KB

The structures 9 and 8 are proposed for the single isolated irradiation product of 5-oxo-5,10-secocholest-I( 10)en-3cc -yl acetate (6) [2] and for the minor product of irradiation of 5-oxo-5,10-secocholest-l(l0)-en-3~ -yl acetate (1) [3], respectively. These compounds are formed in an alternative re