Exploratory studies towards a total synthesis of the unusual bridged tetracyclic Lycopodium alkaloid lycopladine H

Joshua R. Sacher, Steven M. Weinreb

Research output: Contribution to journalArticle

7 Scopus citations

Abstract

A strategy for a total synthesis of the structurally novel Lycopodium alkaloid lycopladine H has been investigated. Key steps that have been tested include: 1. a regioselective DielseAlder cycloaddition of nitroethylene with an o-quinone ketal to produce the bicyclo[2.2.2]octane moiety of the alkaloid; 2. a stereoselective Henry reaction to generate the requisite functionality and configuration at C-5; 3. a stereoselective catalytic hydrogenation of a trisubstituted alkene to set the C-15 methyl configuration.

Original languageEnglish (US)
Pages (from-to)10203-10207
Number of pages5
JournalTetrahedron
Volume67
Issue number52
DOIs
StatePublished - Dec 30 2011

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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