Tetrahedron p. 4099 - 4106 (1993)
Update date:2022-08-25
Topics:
Vasiljeva, Ludmila L.
Manukina, Tatjana A.
Demin, Peter M.
Lapitskaja, Margarita A.
Pivnitsky, Kasimir K.
To characterize the individual epimers of hepoxilin B3, a new total synthesis procedure was developed consisting of subsequent condensations of enentiomerically pure (2R,3S)-epoxy-5-undecynal with LiC≡CCH2Cl and HC≡C(CH2)3COOMe, followed by Lindlar hydrogenation, and finally epimer separation. Derivatives of hepoxilin syn-(10R,11R,12S)-B3 (free acid, methyl ester and acetate of methyl ester) are more polar on silica gel, have negative optical rotations [α]25D -60.6°, -62.6°, -25.2°, respectively, and in 1H NMR spectra have the larger splitting of carbinolic H-10 signal (J10,11 5.0-6.1 Hz). Corresponding values for less polar hepoxilin anti-(10S, 11R,12S)-B3 derivatives are: [α]25D +73.5°, +61.9°, and -2.0°; J10-11 2.95-3.3 Hz. These data suggest that an epimer of hepoxilin B3 recently isolated by W.H.Gerwick et al. from red algae is syn-(10R,11R,12S)-B3.
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