Synthetic studies on ecteinascidin 743: rapid access to the fully functionalized tetrahydroisoquinoline with a bridged 10-membered sulfur containing macrocycle

• Autores: Jieping Zhu, Angèle Chiarioni, Michaël de Paolis
• Localización: Chemical communications, ISSN 1359-7345, Nº. 23, 2003, págs. 2896-2897
• Idioma: inglés
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• Resumen

  • Synthesis of tetrahydroisoquinoline with a 1,4-bridged 10-membered sulfur containing macrolactone (5) is described. Phenolic aldolisation, Pictet¿Spengler cyclisation of an acid sensitive amino diol under newly developed conditions (LiBr, toluene¿TFE, 80 °C) and acid promoted intramolecular C¿S bond formation leading to a 10-membered cycle are key steps of our synthesis