((3Z)-7-methoxycarbonyl-3-heptenyl)-triphenylphosphonium iodide

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CAS: 91097-63-1
MF: C27H30O2P+.HI
MW: 545.41164
Synonyms: ((3Z)-7-methoxycarbonyl-3-heptenyl)-triphenylphosphonium iodide

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Merritt B. Andrus

Brigham Young University
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Co-reporter: Michael A. Christiansen, Merritt B. Andrus
pp: 4805-4808
Publication Date(Web):5 September 2012
DOI: 10.1016/j.tetlet.2012.06.052
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.Image for unlabelled figure