Chen, JinchunChen, XiaochuanBois-Choussy, MicheleZhu, Jieping2010-11-252010-11-252010-11-25200610.1021/ja0571794https://infoscience.epfl.ch/handle/20.500.14299/58453A 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)]Cyclocondensation reaction (Pictet-Spengler; asym. total synthesis of ecteinascidin 743 via diastereoselective Pictet-Spengler condensationdiastereoselective N-alkylationand deprotection/cyclization); Asymmetric synthesis and induction; Cyclization (asym. total synthesis of ecteinascidin 743 via diastereoselective Pictet-Spengler condensationdiastereoselective N-alkylationand deprotection/cyclization); Protective groups (removal; asym. total synthesis of ecteinascidin 743 via diastereoselective Pictet-Spengler condensationdiastereoselective N-alkylationand deprotection/cyclization); Alkylation (stereoselective; asym. total synthesis of ecteinascidin 743 via diastereoselective Pictet-Spengler condensationdiastereoselective N-alkylationand 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 synthesistext::journal::journal article::research article