Organic Letters
Organic Letters
5 years ago

A Stereocontrolled Annulation of the Taccalonolide Epoxy Lactone onto the Molecular Framework of trans-Androsterone

A Stereocontrolled Annulation of the Taccalonolide Epoxy Lactone onto the Molecular Framework of trans-Androsterone
Susan L. Mooberry, April L. Risinger, Jakob Danielsson, Erik J. Sorensen, Xiao-Yang Chen, Diana X. Sun
A robust and scalable route to the taccalonolide skeleton starting from trans-androsterone is presented. The synthesis features a cyclic hydroboration carbonylation reaction, which effectively establishes the trans-hydrindane DE ring junction in a remarkable annulation reaction, as well as a Claisen rearrangement and a catalytic Ullmann-type cyclization. This work is part of a larger effort to uncover new clinical candidates from the taccalonolide class of anticancer agents through advances in chemical synthesis.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02349

DOI: 10.1021/acs.orglett.7b02349

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