Syntheses Totales d'Oxa-9 anthracyclines

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概要

• 論文の詳細を見る

• Racemic 7-hydroxy-9-oxa anthracyclinone (5a) has been synthetised in seven steps from quinizarin (6) and its resolution achieved after glycosylation with 3,4-di-O-acetyl-2-deoxy-L-fucose. Chiral pool syntheses of (8S)-8-hydroxymethyl-9-oxa-anthracyclinone (5b) and of (8S, 10R) and (8S, 10S)-8-hydroxymethyl-10-methyl-9-oxa-anthracyclinones (5c and 5d) have been achieved using (R)-2,3-O-isopropylideneglyceraldehyde (12) and leucoquinizarin (13) as starting materials. Glycosylation of aglycones 5b-5d by either 3,4-di-O-acetyl-2-deoxy-L-fucose or various 3-amino-2,3,6-trideoxy-L-hexoses yielded the corresponding anthracyclines. The synthetic glycosides do not show significant cytotoxic activity at a concentration of 1 μg/ml against L 1210 cells.

• 公益社団法人日本薬学会の論文
• 1989-12-25

著者

• Koch Michel

  Laboratoire De Pharmacognosie De I'universite Rene Descartes U.m.r. C.n.r.s. N° 8638 Faculte De

• Koch M

  Univ. Rene Descartes Paris Fra

• DUFAT-TRINH VAN

  Department de Plarmacognosie de l'Universite Rene Descartes, U.A. au C.N.R.S. n° 484, Faculte de Pha

• SEGUIN Elisabeth

  Department de Plarmacognosie de l'Universite Rene Descartes, U.A. au C.N.R.S. n° 484, Faculte de Pha

• TILLEQUIN Francois

  Department de Plarmacognosie de l'Universite Rene Descartes, U.A. au C.N.R.S. n° 484, Faculte de Pha

• MONNERET Claude

  Department de Plarmacognosie de l'Universite Rene Descartes, U.A. au C.N.R.S. n° 484, Faculte de Pha

• KOCH Michel

  Department de Plarmacognosie de l'Universite Rene Descartes, U.A. au C.N.R.S. n° 484, Faculte de Pha

• Dufat-trinh Van

  Department De Plarmacognosie De L'universite Rene Descartes U.a. Au C.n.r.s. N° 484 Faculte De

• Seguin Elisabeth

  Lab. De Pharmacognosie Ufr De Medecine Pharmacie Rouen

• Tillequin Francois

  Laboratoire De Pharmacognosie De L'universite Paris Descartes

• Tillequin F

  Laboratoire De Pharmacognoise De 1'universite Rene Descartes Umr/cnrsn ^○8638 Faculte Des Scien

• Monneret Claude

  Department De Plarmacognosie De L'universite Rene Descartes U.a. Au C.n.r.s. N° 484 Faculte De

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