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A new strategy for assembly a tricyclic skeleton of ladybirds azaphenalene alkaloids (coccinellides) was developed based on the combination of allylboration reaction and intramolecular metathesis. The first key step is the 1,2-organolithiation of 4-picoline with (4,4-dieth-oxybutyl)lithium with subsequent reductive allylation with triallylborane leading to trans-2-allyl-6-(4,4-diethoxybutyl)-4-methyl-1,2,3,6-tetrahydropyridine...
A four-step synthesis of 11-methyl-13-azabicyclo[7.3.1]trideca-3,10-diene, a potential precursor of the ladybugs´ defensive alkaloids precoccinelline and mirrhine, has been accom-plished. Treatment of 4-picoline with 5-hexenyl-1-lithium, triallylborane, and methanol led to the synthesis of trans-6-allyl-2-(hex-5-enyl)-4-methyl-1,2,3,6-tetrahydropyridine, which reacted with triallylborane upon heating...
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