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

Producción científica: Articlerevisión exhaustiva

7 Citas (Scopus)

Resumen

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.

Idioma originalEnglish (US)
Páginas (desde-hasta)4892-4895
Número de páginas4
PublicaciónOrganic Letters
Volumen19
N.º18
DOI
EstadoPublished - sept 15 2017

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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