Total Synthesis of e nt-Dihydrocorynantheol by Using a Proline-Catalyzed Asymmetric Addition Reaction

Total Synthesis of e nt-Dihydrocorynantheol by Using a Proline-Catalyzed Asymmetric Addition Reaction

9-Tosyl-3,4-dihydro-β-carboline reacted with 3-ethyl-3-buten-2-one in the presence of (S)-proline to give (3R,12bR)-3-ethyl-12-tosyl-3,4,6,7,8,9,10,11,12,12b-decahydro-1H-indolo[2,3-a]quinolizin-2-one in complete enantio- and diastereoselectivity. The compound thus obtained was readily transformed t...

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Veröffentlicht in:Organic letters 2006-04, Vol.8 (8), p.1533-1535
Hauptverfasser: Itoh, Takashi, Yokoya, Masashi, Miyauchi, Keiko, Nagata, Kazuhiro, Ohsawa, Akio
Format: Artikel
Sprache:eng
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Zusammenfassung:9-Tosyl-3,4-dihydro-β-carboline reacted with 3-ethyl-3-buten-2-one in the presence of (S)-proline to give (3R,12bR)-3-ethyl-12-tosyl-3,4,6,7,8,9,10,11,12,12b-decahydro-1H-indolo[2,3-a]quinolizin-2-one in complete enantio- and diastereoselectivity. The compound thus obtained was readily transformed to ent-dihydrocorynantheol in three steps.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0530575