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

De Paolis, Michael; Chiaroni, Angele; Zhu, Jieping

doi:10.1039/b309824a

research article

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

De Paolis, Michael

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Chiaroni, Angele

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Zhu, Jieping

2003

Chemical Communications (ChemComm)

Synthesis of tetrahydroisoquinoline with a 1,4-bridged 10-membered sulfur contg. macrolactone, I (R = CO2CH2CCl3), is described. Phenolic aldolization, Pictet-Spengler cyclization of an acid sensitive amino diol under newly developed conditions (LiBr, toluene-TFE, 80 DegC) and acid promoted intramol. C-S bond formation leading to a 10-membered cycle are key steps of our synthesis. [on SciFinder (R)]