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Abstract

From the ACS meeting Albert I. Meyers was trying to prove something with his approach to the synthesis of griseoviridin, an antibiotic produced by soil microorganisms. Griseoviridin incorporates a D-amino acid. But in nature, L-amino acids are more prevalent than their D-counterparts. Meyers, a chemistry professor at Colorado State University, Fort Collins, considered that griseoviridin might be biosynthesized with an L-amino acid and then somehow later flipped to the observed stereochemistry. It turns out that the molecule is not made that way, as Curt A. Dvorak, a postdoc in Meyers' lab, described at an Organic Chemistry Division symposium on total synthesis of complex molecules. Griseoviridin contains a 23-membered macrocyclic ring that incorporates an oxazole group and a nine-membered lactone that has a vinyl sulfide unit. As Dvorak explained, the molecule was assembled by joining two fragments: one bearing the oxazole group and the other bearing the lactone ring. Syntheses of the two fragments had be...