Total Synthesis of Ecteinascidin 743

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)]


Published in:
Journal of the American Chemical Society, 128, 1, 87-89
Year:
2006
Keywords:
Note:
CAN 144:171144
31-6
Alkaloids
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
0002-7863
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)
Laboratories:




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


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