The glycerol enol ether, fecapentaene-12, is a direct acting fecal mutagen that is
formed in the lower portion of the gastrointestional tract by anaerobic bacteria. The
biological precursor to fecapentaene-12 is a natural product of mammalian origin whose
role in the etiology of colon cancer is unknown.
Preliminary evidence indicated that the precursor may be a plasmalogen with an
intact pentaenol ether moiety. Further structural studies by means of degradative methods
and chromatographic techniques enabled the structure of the precursor to be elucidated.
Based on the structure of the precursor, the name plasmalopentaene-12 was coined.
Synthetic methodology was developed for obtaining synthetic plasmalopentaene12.
This was necessary in order to confirm the structure and to determine the precursor's
biological role. The synthetic methodology proceeded through a novel "acyl migration"
which enables the highly labile pentaenol ether to be generated late in the synthesis. Model
studies indicated that this was a feasible pathway. It was also determined that this
methodology may be highly adaptable to the synthesis of other plasmalogens and may also
provide a new synthetic route to fecapentaene-12.
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