Determination of the absolute configuration of the cytotoxic natural product pericosine D

The synthesis of two diastereomers of pericosine A from (−)-quinic acid was achieved, thus enabling the confirmation of the relative configuration and elucidation of the absolute stereochemistry of cytotoxic natural product pericosine D assigned as methyl (3R,4R,5S,6R)-6-chloro-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate.

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Methyl (3R,4R,5S,6S)-6-chloro-3,4,5-trihydroxy-1-cyclohexene-1-carboxylateC8H11O5Cl[α]D25=-101.0 (c 0.20, EtOH)Chiral source: synthesis from (−)-quinic acidAbsolute configuration: (3R,4R,5S,6S)

Methyl (3R,4R,5S,6R)-6-chloro-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate, (−)-pericosine DC8H11O5Cl[α]D25=-275.4 (c 0.04, EtOH)Chiral source: synthesis from (−)-quinic acidAbsolute configuration: (3R,4R,5S,6R)