Synthesis of the Fire Ant Alkaloids, Solenopsins. A Review

Short Enantioselective Total Syntheses of the Piperidine Alkaloids (S)-Coniine and (2R,6R)-trans-Solenopsin A via Catalytic Asymmetric Imine Hydrosilylation

“…8 The solenopsin alkaloids were the subject of a recent exhaustive review. 9 In addition to numerous routes to racemic trans-solenopsin A, there have also been reports of several asymmetric syntheses, all of which began with optically active amino acids or employed chiral auxiliaries. Our synthesis of trans-solenopsin A (vide infra) is the first to take advantage of a catalytic asymmetric transformation.…”

Recent Advances in Substrate-Controlled Asymmetric Induction Derived from Chiral Pool α-Amino Acids for Natural Product Synthesis

“…Gouault et al accomplished the asymmetric total synthesis of dendrobate alkaloid (+)-241D (74) and isosolenopsin (76) (Scheme 15) [46][47][48]. Structurally, these alkaloids consist of cis-2,6-dialkylpiperidine.…”

Gold‐Catalyzed Hydrofunctionalizations and Spiroketalizations of Alkynes as Key Steps in Total Synthesis

“…Piperidine alkaloid (+)‐241D, from the Panamanian poison frog Dendrobates speciosus , was synthesized from 38 . The constituents of the fire ant Isosolenopsin and Isosolenopsin A could be synthesized from compounds 38 (Isosolenopsin) and 39 (Isosolenopsin A), respectively (Scheme a) . The quinolizidine alkaloid from Vaccinium myrtillus (−)‐Epimyrtine was prepared in a similar manner, albeit slightly elevated temperatures (40 °C) were necessary to drive the reaction …”