Stereostructure reassignment and determination of the absolute configuration of pericosine D(o) by a synthetic
1Laboratory of Pharmaceutical Organic Chemistry, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan. usami@gly.oups.ac.jp
Abstract:
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 OUPS-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) (8) 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.
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Isomers are different chemical species that have the same chemical formula.
Transition metal complexes often exist as geometric isomers, in which the same atoms are connected through the same types of bonds but with differences in their orientation in space. Coordination complexes with two different ligands in the cis and trans positions from a ligand of interest form isomers. For example, the octahedral [Co(NH3)4Cl2]+ ion has two isomers (Figure 1) In the cis...
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