Exploitation of Chiral Epichlorohydrin as Versatile Chiral Building Block

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Epichlorohydrin was obtained practically in enantiomerically pure forms by fermentation in our country. In order to exploit enantiomerically pure epichlorohydrin as versatile chiral building block, we have investigated enantiocontrolled construction of a variety of physiologically active natural products including amino acids, alkaloids, polyketides, terpenes, and steroids. During a 1995-1997 period, we have been engaged in the enantiocontrolled syntheses of "Sporochnol A", the fish deterrent from the Caribbean Marine alge, "carbazoquinocins A and D", the potent lipid peroxidation inhibitors from Streptomyces violaceus 2248-SVT2, "compactin lactone", the essential structural component associated with the biological activity of the potent HMG-CoA reductase compactin, "calcitriol enyne", the a ring component of the activated form of vitamin D,"dihydroxyheliotridane", a physiologically interesting necine base, and "muscarine and three naturally occurring its diastereomers", mushroom poisons exhibiting potent anticholinergic activity. Among these compounds obtained, the absolute configurations of sporochnol A,carbazoquinocins A and D were determined by these syntheses by correlation to the absolute configuration of epichlorohydrin used as the starting material.