Studies on the Development of Practical Electroorganic %reactions Associated with Biological Processes

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Use of chiral building blocks easily accessible from natural bio-mass is of current topics in the synthesis of bio-active compounds. This research project concerns with (A) electrochemical transformations of chiral bio-mass into versatile chiral synthons and their synthetic applications and (B) conversion of biochemically produced penicillin derivatives into the valuable cephalosporin compounds by electrochemical means and their applications. In the research project (A), we developed an efficient functional group preparing methods based on electoorganic reactions, i.e. selenation-deselenation sequence, (2) selective ring rearrangement of oxiranes, (3) ruthenium tetraoxide mediated oxidation of alcohols, (4) halogen mediated ring cleavage of furans, and others. Synthetic utilities of these methodologies are shown in the synthesis of useful bio-active compounds such as karahanaenone from dehydrolynalilyl acetate and chrysanthemic acids from (+)-3-carene, and others. In second research program (B), we have succeeded in the selective ene-type chlorination of prenyl moiety of azetidinones. The procedure has been extended in the practial synthesis of a variety of cepharosporin analogues. Conversion of 3'-chlorocephalosporins into the corresponding 3-methylenecephams is also investigated.