Catalytic N-sulfonyliminium ion-mediated cyclizations to a-vinyl-substituted isoquinolines and beta-carbolines and applications in metathesis

Catalytic Sn(OTf)(2)-induced cyclization of linear, aryl-containing allylic N,O-acetals produced vinyl-substituted tetrahydroisoquinolines and tetrahydro-IH-beta-carbolines. The usefulness of the vinyl moiety in the resulting products was demonstrated via the synthesis of various key building blocks...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 70; no. 14; pp. 5519 - 5527
Main Authors Kinderman, SS, Wekking, MMT, van Maarseveen, JH, Schoemaker, HE, Hiemstra, H, Rutjes, FPJT
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 08.07.2005
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ORGANIC-SYNTHESIS
SHIFT
CARBON
RING-CLOSING METATHESIS
ENANTIOSELECTIVE SYNTHESIS
IMINES
OLEFIN METATHESIS
BISCHLER-NAPIERALSKI
DERIVATIVES
ALKALOIDS
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Summary:Catalytic Sn(OTf)(2)-induced cyclization of linear, aryl-containing allylic N,O-acetals produced vinyl-substituted tetrahydroisoquinolines and tetrahydro-IH-beta-carbolines. The usefulness of the vinyl moiety in the resulting products was demonstrated via the synthesis of various key building blocks for alkaloid structures. The (x-vinyl moiety was utilized in a [2,3] sigmatropic rearrangement, in ring-closing metathesis and a cross-metathesis-based synthesis of vincantril, an antianoxia agent, and a synthetic member of the vincamine type natural products.
ISSN:0022-3263
DOI:10.1021/jo050503t