"BOTPPI, a New Wittig Salt Used in the Synthesis of 12-(S)-Hydroxy-Eico" by Michael A. Christiansen and Merritt B. Andrus
 

Document Type

Article

Journal/Book Title

Tetrahedron Lett.

Publication Date

2012

Volume

53

Issue

36

First Page

4805

Last Page

4808

Abstract

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.

Comments

This manuscript is not the final published version. Please use publisher's citation (below). For published version of this work, please visit:

http://www.sciencedirect.com/science/journal/00404039

Plum Print visual indicator of research metrics
PlumX Metrics
  • Citations
    • Citation Indexes: 8
    • Patent Family Citations: 1
  • Usage
    • Downloads: 406
    • Abstract Views: 34
  • Captures
    • Readers: 14
see details

Included in

Chemistry Commons

Share

COinS
 
 

To view the content in your browser, please download Adobe Reader or, alternately,
you may Download the file to your hard drive.

NOTE: The latest versions of Adobe Reader do not support viewing PDF files within Firefox on Mac OS and if you are using a modern (Intel) Mac, there is no official plugin for viewing PDF files within the browser window.