The Preparation of a Hexacyclic Intermediate for the Synthesis of Strychnos Alkaloids

George A. Kraus; Dan Bougie

doi:10.1055/s-1992-21338

Synlett 1992; 1992(4): 279-280
DOI: 10.1055/s-1992-21338

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The Preparation of a Hexacyclic Intermediate for the Synthesis of Strychnos Alkaloids

George A. Kraus^* , Dan Bougie

^*Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA

Abstract

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The hexacyclic ring system, indolizino[7,8,8a,1-bcd]-pyrido [1,2,3-lm]carbazolone 10 has been synthesized in nine steps from the pyrido[3,2,1-jk]carbazolylethanal 3. Key steps include the selective reduction of aldchyde 3, the stereoselective introduction of an allyl unit via the Sakurai reaction and the ozonolysis/dehydrative cyclization to afford bridgehead enamine 10.

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