ALANYLACTINOBICYCLONE . AN APPLICATION OF COMPUTER TECHNIQUES TO STRUCTURE ELUCIDATION

The structure proof of N-acetylalanylactinobicyclone (1a), a product isolated from the mild basic hydrolysis of N-acetylactinobolin, is described. Evidence was assembled which allowed the formulation of a partial structure, expressed as a set of five structural fragments, which accounted for all the atoms in the molecule. The set of fragments was used as input data for a computer program designed to generate all possible combinations of the fragments, i.e., structures. A total of 11 possible structures were generated, of which eight were eliminated by chemical and spectral data on hand. An nmr study of the mono-O-acetate-d6 derivative of N-acetylalanylactinobicyclone distinguished between the three remaining structural possibilities and permitted the assignment of 4-[N-(N′-acetylalanyl)] amino-3-methyl-9-hydroxy-2-oxabicyclo [3.3.1] nonan-7-one as la. © 1969, American Chemical Society. All rights reserved.