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  4. Asymmetric total syntheses of ecteinascidin 597 and ecteinascidin 583
 
research article

Asymmetric total syntheses of ecteinascidin 597 and ecteinascidin 583

Chen, Jinchun
•
Chen, Xiaochuan
•
Willot, Matthieu
Show more
2006
Angewandte Chemie International Edition

The limited availability of bioactive natural products for pharmaceutical studies and drug development is a problem that can be solved, in principle, by total synthesis. The potent antitumor marine natural products ecteinascidin 597 (I; R = Me) and ecteinascidin 583 (I; R = H) have now been synthesized from readily accessible starting materials in a highly convergent and stereoselective fashion (see scheme). [on SciFinder (R)]

  • Details
  • Metrics
Type
research article
DOI
10.1002/anie.200603179
Author(s)
Chen, Jinchun
Chen, Xiaochuan
Willot, Matthieu
Zhu, Jieping  
Date Issued

2006

Publisher

Wiley-VCH Verlag GmbH

Published in
Angewandte Chemie International Edition
Volume

45

Issue

47

Start page

8028

End page

8032

Subjects

Absolute configuration; Stereoselective synthesis (asym. total syntheses of ecteinascidins 597 and 583); Synthons (chiral; asym. total syntheses of ecteinascidins 597 and 583); Alkaloids Role: SPN (Synthetic preparation)

•

PREP (Preparation) (marine; asym. total syntheses of ecteinascidins 597 and 583)

•

asym synthesis alkaloid ecteinascidin 597 583

Note

CAN 146:252015

31-6

Alkaloids

Institut de Chimie des Substances Naturelles,Gif-sur-Yvette Cedex,Fr.

Journal

written in English.

686776-27-2 ((S)-[3-Hydroxy-4-methoxy-5-methylphenyl]alanol) Role: RCT (Reactant), RACT (Reactant or reagent) (Pictet-Spengler reaction of, with (S)-Garner aldehyde; asym. total syntheses of ecteinascidins 597 and 583); 102308-32-7 ((S)-Garner aldehyde) Role: RCT (Reactant), RACT (Reactant or reagent) (Pictet-Spengler reaction of, with (S)-[3-methoxy-4-methoxy-5-methylphenyl]alanol; asym. total syntheses of ecteinascidins 597 and 583); 17341-93-4 Role: RCT (Reactant), RACT (Reactant or reagent) (asym. total syntheses of ecteinascidins 597 and 583); 184300-07-0P (Ecteinascidin 597); 184300-08-1P (Ecteinascidin 583) Role: SPN (Synthetic preparation), PREP (Preparation) (asym. total syntheses of ecteinascidins 597 and 583); 925451-83-8 Role: RCT (Reactant), RACT (Reactant or reagent) (attempted condensation of, with benzyloxyacetaldehyde and glyoxylate; asym. total syntheses of ecteinascidins 597 and 583); 924-44-7 (Ethyl glyoxylate); 60656-87-3 (2-(Benzyloxy)acetaldehyde) Role: RCT (Reactant), RACT (Reactant or reagent) (attempted condensation of, with isoquinolinylamine piperonyl deriv.; asym. total syntheses of ecteinascidins 597 and 583); 854022-02-9 (N-[2,2,2-Trichloroethoxycarbonyl]-S-(trimethoxytrityl)-L-cysteine) Role: RCT (Reactant), RACT (Reactant or reagent) (esterification of, with bisisoquinoline deriv.; asym. total syntheses of ecteinascidins 597 and 583); 107-21-1 (Ethylene glycol) Role: RCT (Reactant), RACT (Reactant or reagent) (monoprotection of, with Troc-Cl; asym. total syntheses of ecteinascidins 597 and 583); 69404-94-0P (Vanillin tert-butyldimethylsilyl ether) Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and Baeyer-Villiger oxidn. of; asym. total syntheses of ecteinascidins 597 and 583); 925451-98-5P (2-[(2,2,2-Trichloroethoxycarbonyl)oxy]ethanol) Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and Dess-Martin oxidn. of; asym. total syntheses of ecteinascidins 597 and 583); 925451-70-3P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and Grignard reaction of, with methoxybenzenediol Grignard deriv.; asym. total syntheses of ecteinascidins 597 and 583); 874758-58-4P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and N-/O-deisopropylidenation of; asym. total syntheses of ecteinascidins 597 and 583); 925451-89-4P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and N-deprotection of; asym. total syntheses of ecteinascidins 597 and 583); 925451-88-3P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and N-methylation or N-deprotection of; asym. total syntheses of ecteinascidins 597 and 583); 925451-95-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and O-allylation of; asym. total syntheses of ecteinascidins 597 and 583); 925451-73-6P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and O-dealkylation of; asym. total syntheses of ecteinascidins 597 and 583); 925451-87-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and O-deallylation of; asym. total syntheses of ecteinascidins 597 and 583); 925451-79-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and O-deallylation, or Swern oxidn./cyclization and cyanation of; asym. total syntheses of ecteinascidins 597 and 583); 925451-80-5P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and O-deethoxycarbonylation, or O-deallylation/N-deallyloxycarbonylation of; asym. total syntheses of ecteinascidins 597 and 583); 402469-27-6P; 925451-76-9P Role: RC (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and O-methoxymethylation of; asym. total syntheses of ecteinascidins 597 and 583); 925451-77-0P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and Pictet-Spengler reaction of, with O-Troc-glycoaldehyde; asym. total syntheses of ecteinascidins 597 and 583); 925451-78-1P (O-(2,2,2-Trichloroethoxycarbonyl)glycoaldehyde) Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and Pictet-Spengler reaction of, with isoquinolinylmethanamine alpha -benzyl deriv.; asym. total syntheses of ecteinascidins 597 and 583); 925451-85-0P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and S-deprotection of; asym. total syntheses of ecteinascidins 597 and 583); 925451-75-8P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and Swern. oxidn. of; asym. total syntheses of ecteinascidins 597 and 583); 925451-81-6P; 925451-82-7P Role: PRP (Properties), SPN (Synthetic preparation), PREP (Preparation) (prepn. and abs. configuration of; asym. total syntheses of ecteinascidins 597 and 583); 874758-72-2P; 925451-93-0P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and acetylation of; asym. total syntheses of ecteinascidins 597 and 583); 874758-56-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and acylation of, with allyloxycarbonyl chloride; asym. total syntheses of ecteinascidins 597 and 583); 874758-71-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and allylation of; asym. total syntheses of ecteinascidins 597 and 583); 925451-90-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and attempted intramol. cyclization/sulfuration of; asym. total syntheses of ecteinascidins 597 and 583); 925451-92-9P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and deacetylation of; asym. total syntheses of ecteinascidins 597 and 583); 925451-84-9P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and esterification by, of L-cysteine deriv.; asym. total syntheses of ecteinascidins 597 and 583); 259220-89-8P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and ortho-methylation of; asym. total syntheses of ecteinascidins 597 and 583); 925451-96-3P; 925451-97-4P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and oxidative decyanation of; asym. total syntheses of ecteinascidins 597 and 583); 925451-68-9P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn., Grignard formation and aldol reaction of, with isoquinolinylglycinal deriv.; asym. total syntheses of ecteinascidins 597 and 583); 925451-91-8P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn., N-deprotection and desilylation of; asym. total syntheses of ecteinascidins 597 and 583); 925451-86-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn., O-demethoxymethyaltion and intramol. sulfuration/cyclization of; asym. total syntheses of ecteinascidins 597 and 583); 121-33-5 (Vanillin) Role: RCT (Reactant), RACT (Reactant or reagent) (silylation of; asym. total syntheses of ecteinascidins 597 and 583)

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/20.500.14299/58455
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