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Contents Vol 63(12)

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 A , Anthony C. Willis A and Martin G. Banwell A B
+ Author Affiliations
- Author Affiliations

A Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia.

B Corresponding author. Email: mgb@rsc.anu.edu.au

Australian Journal of Chemistry 63(12) 1665-1678 https://doi.org/10.1071/CH10359
Submitted: 30 September 2010  Accepted: 25 October 2010   Published: 6 December 2010

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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