Total Synthesis of Lycopladine A and Carinatine A via a Base-Mediated Carbocyclization

Felix W.W. Hartrampf, Dirk Trauner

Research output: Contribution to journalArticle

Abstract

A concise, enantioselective synthesis of lycopladine A and carinatine A is presented. Our synthetic approach hinges on the recently developed mild carbocyclization of ynones to furnish the hydrindane core of the alkaloids. Their pyridine ring was efficiently installed using the Ciufolini method. Both heterocycles of carinatine A, a rare naturally occurring nitrone, were formed in a single operation.

Original languageEnglish (US)
Pages (from-to)8206-8212
Number of pages7
JournalJournal of Organic Chemistry
Volume82
Issue number15
DOIs
StatePublished - Aug 4 2017

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Hinges
Alkaloids
lycopladine A
hydrindane
pyridine
nitrones

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Total Synthesis of Lycopladine A and Carinatine A via a Base-Mediated Carbocyclization. / Hartrampf, Felix W.W.; Trauner, Dirk.

In: Journal of Organic Chemistry, Vol. 82, No. 15, 04.08.2017, p. 8206-8212.

Research output: Contribution to journalArticle

Hartrampf, Felix W.W. ; Trauner, Dirk. / Total Synthesis of Lycopladine A and Carinatine A via a Base-Mediated Carbocyclization. In: Journal of Organic Chemistry. 2017 ; Vol. 82, No. 15. pp. 8206-8212.
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