Total synthesis of (+/-)-goniomitine via a formal nitrile/donor-acceptor cyclopropane [3 + 2] cyclization.
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.
Morales
Christian L
CL
Department of Chemistry, The University of Western Ontario, London, Ontario, N6A 5B7 Canada.
Pagenkopf
Brian L
BL
D003500:Cyclization; D003521:Cyclopropanes / Q000737:chemistry*; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007769:Lactams / Q000737:chemistry; D008872:Microwaves; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry; D013237:Stereoisomerism
D003521:Cyclopropanes; D026121:Indole Alkaloids; D007769:Lactams; D009570:Nitriles; C526621:goniomitine; C511520:valerolactam