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

Jakob Danielsson, Diana X. Sun, Xiao Yang Chen, April L. Risinger, Susan L. Mooberry, Erik J. Sorensen

Research output: Contribution to journalArticle

3 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)4892-4895
Number of pages4
JournalOrganic Letters
Volume19
Issue number18
DOIs
StatePublished - Sep 15 2017

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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