Synthesis of Functionalized Octahydroindoles Related to Daphnyphyllum Alkaloids

Stéphane Dorich; Juan R. Del Valle; Stephen Hanessian

doi:10.1055/s-0033-1340794

Synlett, Table of Contents

Synlett 2014; 25(6): 799-804
DOI: 10.1055/s-0033-1340794

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Synthesis of Functionalized Octahydroindoles Related to Daphnyphyllum Alkaloids

Stéphane Dorich

Department of Chemistry, Université de Montréal, Station Centre-Ville, C.P. 6128, Montreal, Quebec, H3C 3J7, Canada Fax: +1(514)3435728 Email: stephen.hanessian@umontreal.ca

,

Juan R. Del Valle

Department of Chemistry, Université de Montréal, Station Centre-Ville, C.P. 6128, Montreal, Quebec, H3C 3J7, Canada Fax: +1(514)3435728 Email: stephen.hanessian@umontreal.ca

,

Stephen Hanessian*

Department of Chemistry, Université de Montréal, Station Centre-Ville, C.P. 6128, Montreal, Quebec, H3C 3J7, Canada Fax: +1(514)3435728 Email: stephen.hanessian@umontreal.ca

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Abstract

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Abstract

Functionalized octahydroindoles were synthesized from (±)-cyclohex-2-en-1-ol as potential intermediates for convergent syntheses of several alkaloids from plants of the Daphnyphyllum genus.

Key words

alkaloids - heterocycles - bicyclic compounds - natural products - hydrogenation - diastereoselectivity

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References

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35 Crystallographic data for compounds 9, 11, 17, 27, 28, and 32 have been deposited with the accession numbers CCDC 968290, 968291, 968292, 968293, 968294, and 968295, respectively, and can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk; Web site: www.ccdc.cam.ac.uk/conts/retrieving.html.

Supplementary Material

Supporting Information