Synthetic studies on ecteinascidin 743 (Et 743): asymmetric synthesis of a highly oxygenated tetrahydroisoquinoline via a key phenolic Mannich reaction

A concise synthesis of a highly functionalized, orthogonally protected amino triol I (R = CH2Ph, R1 = SiPh2CMe3) was achieved via a Mannich reaction between a corresponding phenol II and a chiral oxazinone III as a key step. The utility of such an approach is illustrated by a concise synthesis of a highly oxygenated tetrahydroisoquinoline IV (R = CH2Ph), a key structural unit of ecteinascidin 743 (Et 743) and related natural products. [on SciFinder (R)]


Published in:
Synthesis, 23, 4081-4086
Year:
2006
Keywords:
Note:
CAN 146:229494
31-6
Alkaloids
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
0039-7881
written in English.
5437-45-6; 497832-28-7; 924726-98-7 Role: RCT (Reactant), RACT (Reactant or reagent) (asym. synthesis of a highly oxygenated tetrahydroisoquinoline ecteinascidin 743 subunit via a key phenolic Mannich reaction); 924726-97-6P; 924726-99-8P; 924727-00-4P; 924727-01-5P; 924727-02-6P; 924727-03-7P; 924727-04-8P; 924727-05-9P; 924727-06-0P; 924727-09-3P; 924727-10-6P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (asym. synthesis of a highly oxygenated tetrahydroisoquinoline ecteinascidin 743 subunit via a key phenolic Mannich reaction); 114899-77-3P (Ecteinascidin 743); 924727-07-1P; 924727-08-2P Role: SPN (Synthetic preparation), PREP (Preparation) (asym. synthesis of a highly oxygenated tetrahydroisoquinoline ecteinascidin 743 subunit via a key phenolic Mannich reaction)
Laboratories:




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


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