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Transannular Photocyclization of (E)-3B-Acetoxy-5,10-seco-1(10)-cholesten-5-one*

Ljubinka Lorenc ; Department of Chemistry, Faculty of Science, University of Belgrade, Studentski trg 16. P. O. Box 550, YU-11001 Belgrade, Yugoslavia, and Institute of Chemistry, Technology and Metallurgy, Belgrade
Vladimir Pavlović ; Department of Chemistry, Faculty of Science, University of Belgrade, Studentski trg 16. P. O. Box 550, YU-11001 Belgrade, Yugoslavia, and Institute of Chemistry, Technology and Metallurgy, Belgrade
Mihailo Lj. Mihailović ; Department of Chemistry, Faculty of Science, University of Belgrade, Studentski trg 16. P. O. Box 550, YU-11001 Belgrade, Yugoslavia, and Institute of Chemistry, Technology and Metallurgy, Belgrade
Bernard Tinant ; Laboratoire de Chimie physique et de Cristallographie, Universite de Louvain, Butiment Lavoisier, Place Louis Pasteur, 1, B-1348 Louvain-la-Neuve, Belgium
Jean-Paul Declercq ; Laboratoire de Chimie physique et de Cristallographie, Universite de Louvain, Butiment Lavoisier, Place Louis Pasteur, 1, B-1348 Louvain-la-Neuve, Belgium
Maurice Van Meerssche ; Laboratoire de Chimie physique et de Cristallographie, Universite de Louvain, Butiment Lavoisier, Place Louis Pasteur, 1, B-1348 Louvain-la-Neuve, Belgium

Sažetak

UV irradiation of the (E)-5,10-seco-steroidal ketone 1 in acetone
solution results, in addition to the previously describedE/Z isomerization and intramolecular Paterno-Buchi reaction(leading to the la,5:x-oxetane 4 in about 42% yield and 1~,5~-oxetane5 in 2-3% yield), in atransannular cyclization (accompaniedby acetic acid elimination) producing the anthrasteroidal enone 3 (in about 7% yield). The structureof 3 was deduced from spectral data and confirmed by X-ray analysis.

Ključne riječi

Hrčak ID:

175377

URI

https://hrcak.srce.hr/175377

Datum izdavanja:

30.3.1989.

Posjeta: 540 *