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
•
Chiaroni, Angele
•
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)]

Type
research article
DOI
10.1039/b309824a
Author(s)
De Paolis, Michael
Chiaroni, Angele
Zhu, Jieping  
Date Issued

2003

Publisher

Royal Society of Chemistry

Published in
Chemical Communications (ChemComm)
Issue

23

Start page

2896

End page

2897

Subjects

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)

Editorial or Peer reviewed

REVIEWED

Written at

OTHER

EPFL units
LSPN  
Available on Infoscience
November 25, 2010
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/58493