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Synthesis of an intriguing steroidal constitutional isomer

Townsend, D., Shankland, K., Weymouth-Wilson, A., Komsta, Z., Evans, T. and Cobb, A. J. A. (2020) Synthesis of an intriguing steroidal constitutional isomer. Tetrahedron Letters, 61 (23). 151942. ISSN 0040-4039

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To link to this item DOI: 10.1016/j.tetlet.2020.151942


We recently described the synthesis of an unusual tricyclic system, whereby a cis-decalin was fused to a cis-hydrindane. Herein, we wish to describe the elaboration of this system towards steroid-like frameworks. This report describes how, en route to an attempted cardiotonic steroid synthesis, we stereoselectively functionalized the leftmost cyclohexyl ring with an ester ready for steroidal A-ring formation. Ultimately however, the required transposition of the cyclohexylketone did not occur as expected and resulted in the subsequent Robinson annulation forming an unusual steroidal constitutional isomer – the saturated cyclopenta[c]phenanthrene. Remarkably, such unusual tetracyclic connectivity has been reported just once in 70 years.

Item Type:Article
Divisions:Faculty of Life Sciences > School of Chemistry, Food and Pharmacy > School of Pharmacy > Pharmaceutics Research Group
ID Code:90699

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