Synthesis of an intriguing steroidal constitutional isomer

Townsend, D., Shankland, K. ORCID: https://orcid.org/0000-0001-6566-0155, 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 doi: 10.1016/j.tetlet.2020.151942

Abstract/Summary

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
URI	https://reading-clone.eprints-hosting.org/id/eprint/90699
Identification Number/DOI	10.1016/j.tetlet.2020.151942
Refereed	Yes
Divisions	Life Sciences > School of Chemistry, Food and Pharmacy > School of Pharmacy > Pharmaceutics Research Group
Publisher	Elsevier
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