Azomethine Ylide Cycloaddition Approach toward Dendrobine

Synthesis of 5-Deoxymubironine C

Benjamin M. Williams, Dirk Trauner

Research output: Contribution to journalArticle

Abstract

A concise route to the azatricyclo[6.2.1.04,11]undecane core of (-)-dendrobine and (-)-mubironine C is described wherein an unstabilized azomethine ylide cycloaddition provides the complete carbon framework of the natural products. The cyclization precursor is made in short order from (R)-carvone through an unconventional high-pressure Ireland-Claisen reaction. Attempts to install a final hydroxyl group through an intramolecular lactonization strategy and the observation of an unexpected and highly complex enal-ene product are also reported.

Original languageEnglish (US)
Pages (from-to)3061-3068
Number of pages8
JournalJournal of Organic Chemistry
Volume83
Issue number6
DOIs
StatePublished - Mar 16 2018

Fingerprint

Cycloaddition
Cyclization
Biological Products
Hydroxyl Radical
Carbon
undecane
azomethine
dendrobine
carvone

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Azomethine Ylide Cycloaddition Approach toward Dendrobine : Synthesis of 5-Deoxymubironine C. / Williams, Benjamin M.; Trauner, Dirk.

In: Journal of Organic Chemistry, Vol. 83, No. 6, 16.03.2018, p. 3061-3068.

Research output: Contribution to journalArticle

Williams, Benjamin M. ; Trauner, Dirk. / Azomethine Ylide Cycloaddition Approach toward Dendrobine : Synthesis of 5-Deoxymubironine C. In: Journal of Organic Chemistry. 2018 ; Vol. 83, No. 6. pp. 3061-3068.
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