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

• Published in: Synthesis, num. 23, p. 4081-4086
• Publication date: 2006

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)]

Keywords: Mannich reaction (asym. synthesis of a highly oxygenated tetrahydroisoquinoline ecteinascidin 743 subunit via a key phenolic Mannich reaction); Alkaloids Role: SPN (Synthetic preparation) ; PREP (Preparation) (isoquinoline; asym. synthesis of a highly oxygenated tetrahydroisoquinoline ecteinascidin 743 subunit via a key phenolic Mannich reaction); Stereoselective synthesis (of a highly oxygenated tetrahydroisoquinoline ecteinascidin 743 subunit via a key phenolic Mannich reaction) ; ecteinascidin 743 subunit asym synthesis phenolic Mannich reaction; tetrahydroisoquinoline ecteinascidin 743 subunit asym synthesis phenolic Mannich reaction; alkaloid ecteinascidin 743 subunit asym synthesis phenolic Mannich reaction

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)

Reference

• EPFL-ARTICLE-158099

Record created on 2010-11-25, modified on 2017-05-12