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Issue 23, 2003
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Synthetic studies on ecteinascidin 743: rapid access to the fully functionalized tetrahydroisoquinoline with a bridged 10-membered sulfur containing macrocycle

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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.

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

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Publication details

The article was received on 15 Aug 2003, accepted on 06 Oct 2003 and first published on 20 Oct 2003


Article type: Communication
DOI: 10.1039/B309824A
Citation: Chem. Commun., 2003,0, 2896-2897
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    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 and J. Zhu, Chem. Commun., 2003, 0, 2896
    DOI: 10.1039/B309824A

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