BOTPPI, a New Wittig Salt Used in the Synthesis of 12-(S)-Hydroxy-Eicosatetraenoic Acid [12-(S)-HETE]
An efficient route to (Z)-(8-benzyloxy-8-oxooct-3-en-1-yl)triphenylphosphonium iodide, or BOTPPI, is disclosed, complete with full experimental details, NMR spectra, and HRMS data. BOTPPI serves as a surrogate for (Z)-(8-methoxy-8-oxooct-3-en-1-yl)triphenylphosphonium iodide, or MOTPPI, a Wittig salt previously used in two 12-HETE syntheses. BOTPPI has the advantage over MOTPPI of being derived from a sequence for which every intermediate is UV-active and amenable to large-scale chromatographic purification. A formal asymmetric total synthesis of 12-(S)-HETE is also reported, involving a stereoselective phase-transfer catalyzed (PTC) alkylation in its key step.
Christiansen, M. A.; Andrus, M. B. “BOTPPI, a New Wittig Salt Used in the Synthesis of 12-(S)-Hydroxy-Eicosatetraenoic Acid [12-(S)-HETE].” Tetrahedron Lett. 2012, 53, 4805-4808.
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