Stereostructure Reassignment and Determination of the Absolute Configuration of Pericosine Do by a Synthetic Approach

A combination,of chemical synthesis and NMR methods was used to reassign the structure of pericosine D-o (8), a cytotoxic marine natural Product produced by the fungus Periconia byssoides OUP-N133 that was originally derived from the sea hare Aplysia kurodai. Chemical synthesis was used to prepare pericoisne D-o (8) from a known chlorohydrin. that was in turn derived from (-)-quinic acid. The absolute configuration of natural pericosine D-o (B) was determined to be methyl (3R,4S,5S,6S)-6-chloro-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate. HPLC. analyses using a chiral-phase column indicated that Pericosine D-o (8) exists in an enantiomerically pure form in nature.