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research article

Total Synthesis of Ecteinascidin 743

Chen, Jinchun
•
Chen, Xiaochuan
•
Bois-Choussy, Michele
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2006
Journal of the American Chemical Society

A convergent total synthesis of ecteinascidin 743 is realized from five building blocks of almost equal size. It takes 23 steps from L-3-hydroxy-4-methoxy-5-Me phenylalanol (I) with an overall yield of 3%. The most notable features include (a) rapid construction of the D-E segment by highly diastereoselective Pictet-Spengler condensation of Garner's aldehyde with I, (b) diastereoselective N-alkylation of racemic benzyl bromide II by enantiomerically pure amino alc. III, and (c) one-pot deprotection/cyclization of the S-protected precursor IV leading to a 1,4-bridged 10-membered ring. [on SciFinder (R)]

  • Details
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Type
research article
DOI
10.1021/ja0571794
Author(s)
Chen, Jinchun
•
Chen, Xiaochuan
•
Bois-Choussy, Michele
•
Zhu, Jieping  
Date Issued

2006

Published in
Journal of the American Chemical Society
Volume

128

Issue

1

Start page

87

End page

89

Subjects

Cyclocondensation reaction (Pictet-Spengler; asym. total synthesis of ecteinascidin 743 via diastereoselective Pictet-Spengler condensation

•

diastereoselective N-alkylation

•

and deprotection/cyclization); Asymmetric synthesis and induction; Cyclization (asym. total synthesis of ecteinascidin 743 via diastereoselective Pictet-Spengler condensation

•

diastereoselective N-alkylation

•

and deprotection/cyclization); Protective groups (removal; asym. total synthesis of ecteinascidin 743 via diastereoselective Pictet-Spengler condensation

•

diastereoselective N-alkylation

•

and deprotection/cyclization); Alkylation (stereoselective; asym. total synthesis of ecteinascidin 743 via diastereoselective Pictet-Spengler condensation

•

diastereoselective N-alkylation

•

and deprotection/cyclization)

•

ecteinascidin 743 asym total synthesis; Pictet Spengler condensation ecteinascidin 743 asym total synthesis; diastereoselective N alkylation ecteinascidin 743 asym total synthesis; deprotection cyclization ecteinascidin 743 asym total synthesis

Note

CAN 144:171144

31-6

Alkaloids

Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.

Journal

written in English.

533-31-3 (1,3-Benzodioxol-5-ol); 645-33-0; 924-44-7 (Ethyl glyoxylate); 2937-50-0; 17763-80-3; 102308-32-7 (Garner's aldehyde); 686776-27-2; 854022-02-9 Role: RCT (Reactant), RACT (Reactant or reagent) (asym. total synthesis of ecteinascidin 743 via diastereoselective Pictet-Spengler condensation, diastereoselective N-alkylation, and deprotection/cyclization); 111726-43-3P; 114899-80-8P (Ecteinascidin 770); 244126-41-8P; 308359-33-3P; 366020-68-0P; 366020-69-1P; 874758-51-7P; 874758-53-9P; 874758-54-0P; 874758-55-1P; 874758-56-2P; 874758-58-4P; 874758-59-5P; 874758-61-9P; 874758-63-1P; 874758-64-2P; 874758-65-3P; 874758-66-4P; 874758-67-5P; 874758-68-6P; 874758-69-7P; 874758-70-0P; 874758-71-1P; 874758-72-2P; 874758-73-3P; 874758-74-4P; 874758-76-6P; 874758-78-8P; 874758-82-4P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (asym. total synthesis of ecteinascidin 743 via diastereoselective Pictet-Spengler condensation, diastereoselective N-alkylation, and deprotection/cyclization); 114899-77-3P (Ecteinascidin 743); 874758-57-3P; 874758-60-8P; 874758-62-0P Role: SPN (Synthetic preparation), PREP (Preparation) (asym. total synthesis of ecteinascidin 743 via diastereoselective Pictet-Spengler condensation, diastereoselective N-alkylation, and deprotection/cyclization)

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/20.500.14299/58453
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