Synthesis of some bisquaternary salts of the alkaloids loline and lolinine

Synthesis of (±)-Acetylnorloline via Stereoselective Tethered Aminohydroxylation

“…In addition to insecticidal properties, the most abundant alkaloid, loline 1, also exhibits modest antitumor 4 activity and related derivatives of 1 are muscle relaxants. 5 The lolines are polycyclic pyrrolizidine alkaloids 6 featuring an exo amine at C1 and a strained bridgehead ether connecting C2 and C7. The C1-amine is found with various alkyl and acyl substitutions.…”

“…This mutualistic relationship between specific grasses and fungi is a long-standing natural pest control paradigm, and because of low mammalian toxicity, there is potential to use lolines as natural commercial insecticides. In addition to insecticidal properties, the most abundant alkaloid, loline 1 , also exhibits modest antitumor activity and related derivatives of 1 are muscle relaxants …”