Total synthesis of Amaryllidaceae alkaloids, (+)-vittatine and (+)-haemanthamine, starting from d-glucose

Masahiro Bohno, Kazuteru Sugie, Hidetoshi Imase, Yusralina Binti Yusof, Takeshi Oishi, Noritaka Chida

研究成果: Article査読

43 被引用数 (Scopus)

抄録

The stereoselective total synthesis of (+)-vittatine 1 and (+)-haemanthamine 2 starting from d-glucose is described. The cyclohexene ring in 1 was prepared in an optically active form from d-glucose using Ferrier's carbocyclization reaction, and the critical quaternary carbon was stereoselectively generated via chirality transfer by the Claisen rearrangement of cyclohexenol 6. The hexahydroindole skeleton was effectively constructed by the intramolecular aminomercuration-demercuration of 14, followed by Chugaev reaction to provide 16. Finally, Pictet-Spengler reaction completed the first chiral synthesis of (+)-vittatine 1. On the other hand, the α-hydroxylation of the ester 5 stereoselectively proceeded to give α-hydroxy ester 19, to which was introduced an amino function to provide 4. A similar transformation of 4, as employed in the synthesis of vittatine, furnished (+)-haemanthamine 2.

本文言語English
ページ(範囲)6977-6989
ページ数13
ジャーナルTetrahedron
63
30
DOI
出版ステータスPublished - 2007 7 23

ASJC Scopus subject areas

  • 生化学
  • 創薬
  • 有機化学

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