COMPASS Program - An Original Semi-Emperical Approach To Computer-Assisted Synthesis

Abstract

The fundamental principle of the original “DIssection-Approximation” approach (DIA-approach) to the formal description of organic reactions are presented. It is shown that organic reactions can be considered as dissections of chemical bonds followed by the appropriate “approximations” of the reaction centers around the dissected bonds. A new original COMPASS program for computer-assisted organic synthesis (CAOS) has been developed for IBM PC on the basis of DIA-approach. The COMPASS program is shown to be a reasonable compromise between two traditional (empirical and nonempirical) directions in CAOS. We have considered the approach which has been developed as an individual semi-empirical direction in CAOS. The main feature of this semi-empirical approach is shown to be the combination of pure combinatorial methods with a small knowledge base that includes empirical rules in their most generalized form. The powerful ability of the COMPASS program to reproduce the key skeleton transformations in the total syntheses of natural compound is demonstrated for the structures quadrone and sirein.