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Total synthesis of (+/-)-hapalindole Q
1Department of Chemistry, University of Western Ontario, London, Ontario N6A 5B7, Canada.
Organic Letters
|September 28, 2001
Abstract:
[reaction: see text] The total synthesis of the antibacterial and antimycotic alkaloid hapalindole Q has been achieved in eight steps and 12.4% overall yield. The key step involves a regio- and diastereoselective Diels-Alder reaction to afford a bicyclo[2.2.2]oct-2-ene. This cycloadduct was subsequently dihydroxylated, cleaved, and converted to the natural product.