Synthetic studies on ecteinascidin 743: rapid access to the fully functionalized tetrahydroisoquinoline with a bridged 10-membered sulfur containing macrocycle.
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 degrees C) and acid promoted intramolecular C-S bond formation leading to a 10-membered cycle are key steps of our synthesis.
De Paolis
Michaël
M
Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette, France.
Chiaroni
Angèle
A
Zhu
Jieping
J