Synthetic studies on ecteinascidin 743: rapid access to the fully functionalized tetrahydroisoquinoline with a bridged 10-membered sulfur containing macrocycle
Literature Information
Michaël De Paolis, Angèle Chiaroni, Jieping Zhu
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.
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![1-oxaspiro[4.4]nonan-6-one structure 1-oxaspiro[4.4]nonan-6-one structure](https://static.chemtradehub.com/structs/134/134179-01-4-e051.webp)
