Total synthesis of (±)-goniomitine via a formal nitrile/donor- acceptor cyclopropane [3 + 2] cyclization

Article abstract of DOI:10.1021/ol702376j

(Chemical Equation Presented) The total synthesis of (±)-goniomitine has been accomplished in 17 linear steps with 5.2% overall yield starting from commercially available δ-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.