Total synthesis of (+/-)-goniomitine via a formal nitrile/donor-acceptor cyclopropane [3 + 2] cyclization |
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Authors: | Morales Christian L Pagenkopf Brian L |
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Institution: | Department of Chemistry, The University of Western Ontario, London, Ontario, N6A 5B7 Canada. |
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Abstract: | The total synthesis of (+/-)-goniomitine has been accomplished in 17 linear steps with 5.2% overall yield starting from commercially available delta-valerolactam. A synthetic highlight includes the first application of a formal 3 + 2] cycloaddition between a highly functionalized nitrile and a donor-acceptor cyclopropane to prepare an indole nucleus. The use of a microwave reactor is shown to greatly improve the reaction times for two steps. |
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