Thc reactions leading to the establishment of structure I for lycopodine are discussed. S t r u c t~~r e s are proposed for three cyclizatioll products derived from lycopodine.I n a short comlnunication (1) we proposed structure I for lycopodine. This structure has been confirmed by the worlt of Anet (2), who succeeded in interconverting several Lycopodiz~m alkaloids, among which was lycopodine. In this paper we wish to give a full account of our worlt on the elucidation of the structure of the alltaloid and t o discuss the structures of the tetracylic compounds obtained on elimination of hydrogen halide from lycopodine methiodide and a-and P-cyanobromolycopodine.
A novel class of insecticides, the dihydrooxadiazines, was proposed following the use of molecular modelling techniques. These compounds represent conformationally restricted analogues of octopamine. Eight dihydrooxadiazines were synthesized and evaluated for useful insecticidal properties. Several of these compounds demonstrated activity against rice planthoppers, mite eggs, and tobacco budworm eggs.
Abstract:The crystal structure of 2-(4-bromophenyl)-4-(2-fluoroethyl)-5,6-dihydro-4H-1,3,4-oxadiazine hydrochloride, a new octopamine agonist, has been established by Patterson and Fourier methods and refined to a final R value of 0.0293 for 2123 absorption-corrected observed data. The crystals are monoclinic, n = 14.336(3), b = 12.649(3), c = 6.989(1) A, P = 93.48(1)", and the space group is P2,lc. Its structural similarities with the crystal structure of the invertebrate neurotransmitter, octopamine, are described and support the hypothesis that the pesticidal properties of dihydrooxadiazines are, at least partially, due to perturbation of octopaminergic systems.Key words: dihydrooxadiazine, octopamine agonist.
Information pertaining to the position of the carbonyl group relative t o the nitrogen atorn a n d to the size of one of the nitrogen rings in lycopodine has been obtained through n study of the reactions of a-arrcl 8-cyanobro~nolycopodine.
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