Synthetic studies on ecteinascidin 743: rapid access to the fully functionalized tetrahydroisoquinoline with a bridged 10-membered sulfur containing macrocycle
2003
Abstract
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)]
Details
Title
Synthetic studies on ecteinascidin 743: rapid access to the fully functionalized tetrahydroisoquinoline with a bridged 10-membered sulfur containing macrocycle
Author(s)
De Paolis, Michael ; Chiaroni, Angele ; Zhu, Jieping
Published in
Chemical Communications
Issue
23
Pages
2896-2897
Date
2003
ISSN
1359-7345
Keywords
Cyclocondensation reaction (Pictet-Spengler; 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); Crystal structure; Molecular structure (of a phenolic tetrahydroisoquinoline); Asymmetric synthesis and induction (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); Aldol condensation (stereoselective; 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); ecteinascidin 743 tetrahydroisoquinoline sulfur macrolactone fragment prepn; phenolic aldolization Pictet Spengler cyclization tetrahydroisoquinoline macrolactone prepn
Note
CAN 140:164059
31-6
Alkaloids
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
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)
31-6
Alkaloids
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
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
LSPN
Record Appears in
Scientific production and competences > SB - School of Basic Sciences > ISIC - Institute of Chemical Sciences and Engineering > LSPN - Laboratory of synthesis and natural products
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Published
Peer-reviewed publications
Work outside EPFL
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Record creation date
2010-11-25