Structural and Synthetic Studies on Lycopodium Alkaloids

Abstract

<p> An investigation of flabelliformine, an alkaloid obtained from Lycopodium flabelliforme, led to the establishment of its structure. </p> <p> A study of the mass spectra of annotine (a minor alkaloid present in Lycopodium annotinum) and several of its derivatives in combination with degradative work gave support to a total structure proposed previously for the alkaloid.</p> <p> A synthetic approach to the Lycopodium alkaloids was considered. 1-Carbomethoxy-3-methyl-7-methoxybicyclo [3.3.1] non-3-en-9-one, a compound which appeared suitable as an intermediate in the synthesis, was prepared in low yield. The difficulty encountered in the purification of this compound, coupled with the low yield in which it was obtained, indicated the impracticality of this approach to a total synthesis of a Lycopodium alkaloid.</p>