The steroidal motif is a highly privileged structure in medicinal chemistry and, as such, expedient access to steroids and steroidal derivatives is highly desirable to the synthetic community. We envisaged that the core ring structure of these complex frameworks could be rapidly generated through a one-pot Suzuki-Miyaura (SM), Diels-Alder (DA) approach using dinucleophilic species <b>1 </b>(Scheme 1). In order to achieve this, discrimination between competing SM and Heck pathways of <b>1 </b>had to be established. Here we report discrimination between competing synthetic pathways can be controlled by exploiting a subtle change in the basic reaction media, generating a platform for cascade events to expediently access molecular complexity. A range of substituted cyclohexene 3D frameworks were synthesized through this methodology as well as construction of a biologically relevant steroidal core.

One-pot cascade Suzuki-Miyaura/Diels-Alder approach to steroidal cores enabled by nucleophile chemoselectivity

254th National Meeting (2017)

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