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Total synthesis of 11(R,S)-HETE (13)

✍ Scribed by George Just; Corinne Luthe

Publisher
Elsevier Science
Year
1982
Tongue
French
Weight
192 KB
Volume
23
Category
Article
ISSN
0040-4039

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✦ Synopsis

An expedient preparation of ll(R,S)-HETE which may be adapted to the synthesis of 11(S)-HETE is described.

Corey and Kang' recently described the synthesis of 11(R)-HETE (s), which could serve as a precursor to the corresponding hydroperoxide 14 or peroxy-radical Is, substances implicated in prostaglandin biosynthesis'.

We wish to report an alternate synthesis of ll(R,S)-HETE, which, since glycidol is available as the R isomer3, constitutes a formal synthesis of S-s, the enantiomer of opposite configuration to that described by Corey, and probably a better precursor for the preparation of 11(R)-HPETE.

To suitably protected propargyl alcohol 1 _4 (60 nun011 in THF (60 ml) at 5' was added first n-butyllithium (55 mmol) and then glycidol derivative 2 5

πŸ“œ SIMILAR VOLUMES

Total enantiospecific synthesis of 12(r)
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All chemical yields refer to chromatographically homogeneous products. All new compounds exibited satisfactory spectral (IR, NMR, and mass ) data.

Total synthesis of (11R, 12S)-diHETE
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The first total synthesis of (1 lR, 12s) diHETE IS reported. The key step is the highly chemioand stereaselective osmylation of a double bond in a trienyne system selectively complexed by an Fe(CO)3 group.