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Synthesis, properties, and identification of epimeric hepoxilins (−)-(10R)-B3 and (+)-(10S)-B3

✍ Scribed by Ludmila L. Vasiljeva; Tatjana A. Manukina; Peter M. Demin; Margarita A. Lapitskaja; Kasimir K. Pivnitsky

Publisher
Elsevier Science
Year
1993
Tongue
French
Weight
702 KB
Volume
49
Category
Article
ISSN
0040-4020

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✦ Synopsis

Abetract' To characterise the individual epimers of hepoxilin Bs, a new total synthesis procedure was developed consisting of subsequent condensations of enantromerically pure (2R,3S)-epoxy-5-undecynal with LiCmXXxCl and HCrC(C?iz)aC~Me, followed by Lindlar hydrogenation, and finally epimer separation. Derivatives of hepoxihn m-(lOR,llR,lZS)-Bs (free acid, methyl ester and acetate of methyl ester) are more polar on silica gel, have negative optical rotations [a]% -60.S0, -62.60, -25.P, respectively, and in 1R NMR spectra have the larger splitting of carbinolic H-10 signal (JIo,,u 5.0-6.1 Hz). Corresponding values for less polar hepoxilin ~(lOS,llR,12S)-BJ derivatives are: [a]% t73.50, t61.9, and -2.00; Jr&n 2.95-3.3 Hz. These data suggest that an epimer of hepoxilin Bs recently isolated by W.H.Gerwick et al. from red algae is m-(lOR,llR,12S)-Bs.

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