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Concise asymmetric syntheses of (+)- and (-)-tetraponerine-8, (+)- and (-)- tetraponerine-7, and their ethyl homologues. A correction of the structures of tetraponerine-3, and -7

par Macours, Pascale ;Braekman, Jean Claude ;Daloze, Désiré
Référence Tetrahedron, 51, 5, page (1415-1428)
Publication Publié, 1995

Article révisé par les pairs

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Résumé :

(+)- and (-)-T-8, (+)- and (-)-9-epi-T-8, and their ethyl homologues were synthesized in six steps and 27% overall yield from chiral acetylenic sulfoxide (+)-7a or (+)-7b, via a cycloaddition reaction with 3,4,5,6-tetrahydropyridine-1-oxide, and chromatographic separation of the resulting diastereoisomeric Δ4-isoxazolines. Comparison of the spectral properties of the synthetic (+)-9-epi-T-8 with those of natural (+)-T-7 and (+)-T-3 led us to correct the structures of the latter two compounds. The absolute configuration of (+)-T-4 was determined to be 5R,9S,11R, and those of (+)-T-7 and (+)-T-3 to be 5R,9R,11R by comparison of their CD curves with those of the synthetic compounds.