Total Synthesis of (±)-Herbindole B and (±)-cis-Trikentrin B
Authors:
- 1 March 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 7 (7) , 1215-1218
Abstract
Herbindole B and cis-trikentrin B are naturally occurring indoles having the unusual and synthetically challenging pattern of carbon substitution at the 4−7 and 5−7 positions, respectively, with no substitution at the 1−3 positions. The total syntheses of these polyalkylated indoles have been achieved in 19 and 12 steps, respectively. The synthesis of herbindole B relies on two iterations of a quinine monoimine Diels−Alder reaction, while cis-trikentrin B uses a single cycloaddition of a suitable quinone monoimine. Indolization of the adducts provides suitably substituted benzopyrrole nuclei for elaboration to the natural products.Keywords
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