The Pd-catalyzed Alder-ene reactions of N-protected and propargylated 1-amino-2-aryl-2-cyclohexenes as a new route to C3a-arylhexahydroindoles: Towards the total synthesis of tazettine

Anna L. Lehmann; Anthony C. Willis; Martin G. Banwell

doi:10.1071/CH10359

The Pd-catalyzed Alder-ene reactions of N-protected and propargylated 1-amino-2-aryl-2-cyclohexenes as a new route to C3a-arylhexahydroindoles: Towards the total synthesis of tazettine

Anna L. Lehmann, Anthony C. Willis, Martin G. Banwell

Research output: Contribution to journal › Article › peer-review

22 Citations (Scopus)

Abstract

A series of N-protected and propargylated 1-amino-2-aryl-2-cyclohexenes (4) has been prepared. Several of these have been shown to undergo an intramolecular Alder-ene reaction in the presence of palladium acetate and the ligand BBEDA to afford C3a-arylhexahydroindoles of the general form 1. Certain of these products may serve as precursors to the alkaloid tazettine (2).

Original language	English
Pages (from-to)	1665-1678
Number of pages	14
Journal	Australian Journal of Chemistry
Volume	63
Issue number	12
DOIs	https://doi.org/10.1071/CH10359
Publication status	Published - 2010

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abstract = "A series of N-protected and propargylated 1-amino-2-aryl-2-cyclohexenes (4) has been prepared. Several of these have been shown to undergo an intramolecular Alder-ene reaction in the presence of palladium acetate and the ligand BBEDA to afford C3a-arylhexahydroindoles of the general form 1. Certain of these products may serve as precursors to the alkaloid tazettine (2).",

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The Pd-catalyzed Alder-ene reactions of N-protected and propargylated 1-amino-2-aryl-2-cyclohexenes as a new route to C3a-arylhexahydroindoles: Towards the total synthesis of tazettine. / Lehmann, Anna L.; Willis, Anthony C.; Banwell, Martin G.
In: Australian Journal of Chemistry, Vol. 63, No. 12, 2010, p. 1665-1678.

Research output: Contribution to journal › Article › peer-review

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AB - A series of N-protected and propargylated 1-amino-2-aryl-2-cyclohexenes (4) has been prepared. Several of these have been shown to undergo an intramolecular Alder-ene reaction in the presence of palladium acetate and the ligand BBEDA to afford C3a-arylhexahydroindoles of the general form 1. Certain of these products may serve as precursors to the alkaloid tazettine (2).

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The Pd-catalyzed Alder-ene reactions of N-protected and propargylated 1-amino-2-aryl-2-cyclohexenes as a new route to C3a-arylhexahydroindoles: Towards the total synthesis of tazettine

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