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

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

Chen, Xiaochuan
•
Chen, Jinchun
•
Zhu, Jieping  
2006
Synthesis

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)]

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Type
research article
DOI
10.1055/s-2006-950343
Author(s)
Chen, Xiaochuan
Chen, Jinchun
Zhu, Jieping  
Date Issued

2006

Published in
Synthesis
Issue

23

Start page

4081

End page

4086

Subjects

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

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)

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/20.500.14299/58454
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