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 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)]


Published in:
Chemical Communications, 23, 2896-2897
Year:
2003
Keywords:
Note:
CAN 140:164059
31-6
Alkaloids
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
1359-7345
written in English.
114899-77-3P (Ecteinascidin 743) Role: PNU (Preparation, unclassified), PREP (Preparation) (prepn. of the tetrahydroisoquinoline with a bridged 10-membered sulfur contg. macrocycle from sesamol via phenolic aldolization and Pictet-Spengler cyclization towards the synthesis of ecteinascidin 743); 654644-01-6P Role: PRP (Properties), SPN (Synthetic preparation), PREP (Preparation) (prepn. of the tetrahydroisoquinoline with a bridged 10-membered sulfur contg. macrocycle from sesamol via phenolic aldolization and Pictet-Spengler cyclization towards the synthesis of ecteinascidin 743); 106-95-6; 533-31-3 (1,3-Benzodioxol-5-ol); 96845-11-3 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of the tetrahydroisoquinoline with a bridged 10-membered sulfur contg. macrocycle from sesamol via phenolic aldolization and Pictet-Spengler cyclization towards the synthesis of ecteinascidin 743); 111726-43-3P; 187040-02-4P; 187040-03-5P; 654643-96-6P; 654643-97-7P; 654643-98-8P; 654643-99-9P; 654644-00-5P; 654644-02-7P; 654644-03-8P; 654644-04-9P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of the tetrahydroisoquinoline with a bridged 10-membered sulfur contg. macrocycle from sesamol via phenolic aldolization and Pictet-Spengler cyclization towards the synthesis of ecteinascidin 743); 654643-95-5P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of the tetrahydroisoquinoline with a bridged 10-membered sulfur contg. macrocycle from sesamol via phenolic aldolization and Pictet-Spengler cyclization towards the synthesis of ecteinascidin 743)
Laboratories:




 Record created 2010-11-25, last modified 2018-03-17


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