THE ALKALOIDS OF LYCOPODIUM ANNOTINUM: PART V. THE STRUCTURE AND STEREOCHEMISTRY OF LYCOFOLINE

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Abstract
Lycofoline forms a monoacetyl or a diacetyl derivative, depending on the reaction conditions. Hydrogenation of lycofoline yields dihydrolycofoline. Sodium borohydride reduction of acrifoline under non-epimerizing conditions gives the known acrifolinol, but reduction in the presence of sodium hydroxide gives both acrifolinol and lycofoline. From these reactions as well as the evidence of n.m.r. spectra, lycofoline is shown to have structure IV.

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