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

M De Paolis, A Chiaroni, J Zhu

Index: De Paolis, Michael; Chiaroni, Angele; Zhu, Jieping Chemical Communications, 2003 , # 23 p. 2896 - 2897

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Abstract

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.