Total synthesis of the tetracyclic antimalarial alkaloid (±)-Myrioneurinol

Anthony J. Nocket, Steven M. Weinreb

Research output: Contribution to journalArticle

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Abstract

The first total synthesis of the tetracyclic antimalarial Myrioneuron alkaloid (±)-myrioneurinol has been accomplished using three highly diastereoselective reactions as pivotal steps: 1) an intramolecular Michael addition of a benzyloxycarbonyl-protected lactam titanium enolate to an α,β-unsaturated ester for construction of the spirocyclic C5 quaternary center and the a/d rings, 2) a malonate anion conjugate addition to a transient nitrosoalkene to install the requisite functionality and configuration at the C7 position, and 3) an intramolecular sulfonyliminium aza-Sakurai reaction to form the b ring and the attendant C9/C10 configuration of the natural product.

Original languageEnglish (US)
Pages (from-to)14162-14165
Number of pages4
JournalAngewandte Chemie - International Edition
Volume53
Issue number51
DOIs
StatePublished - Dec 15 2014

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All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

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