Synthetic studies on ecteinascidin 743: rapid access to the fully functionalized tetrahydroisoquinoline with a bridged 10-membered sulfur containing macrocycle

Literature Information

Publication Date 2003-10-20
DOI 10.1039/B309824A
Impact Factor 6.222
Authors

Michaël De Paolis, Angèle Chiaroni, Jieping Zhu


View Original

Abstract

Synthesis of tetrahydroisoquinoline with a 1,4-bridged 10-membered sulfur containing macrolactone (5) is described. Phenolic aldolisation, Pictet–Spengler cyclisation of an acid sensitive amino diol under newly developed conditions (LiBr, toluene–TFE, 80 °C) and acid promoted intramolecular C–S bond formation leading to a 10-membered cycle are key steps of our synthesis.

Related Literature

Mesoscopic modeling of Li insertion in phase-separating electrode materials: application to lithium iron phosphate

Mohammad Farkhondeh, Mark Pritzker, Michael Fowler, Mohammadhosein Safari, Charles Delacourt

2014-09-09 Paper

DOI: 10.1039/C4CP03530E

Capture of heliophobic atoms by 4He nanodroplets: the case of cesium

Antonio Leal, David Mateo, Alberto Hernando, Martí Pi, Manuel Barranco

2014-09-22 Paper

DOI: 10.1039/C4CP03297G

Polarisation charge switching through the motion of metal atoms trapped in fullerene cages

G. Raggi, A. J. Stace, E. Bichoutskaia

2014-09-24 Paper

DOI: 10.1039/C4CP02672A

Physicochemical properties of pentaglyme–sodium bis(trifluoromethanesulfonyl)amide solvate ionic liquid

Shoshi Terada, Toshihiko Mandai, Risa Nozawa, Kazuki Yoshida, Kazuhide Ueno, Seiji Tsuzuki, Masayoshi Watanabe

2014-04-25 Paper

DOI: 10.1039/C4CP00746H

Back cover

Cover

DOI: 10.1039/C4CP90156H

Atomic charge transfer-counter polarization effects determine infrared CH intensities of hydrocarbons: a quantum theory of atoms in molecules model

Arnaldo F. Silva, Wagner E. Richter, Helen G. C. Meneses, Roy E. Bruns

2014-09-25 Paper

DOI: 10.1039/C4CP02922D

Complexation of DNA with ruthenium organometallic compounds: the high complexation ratio limit

Stéphane Despax, Fuchao Jia, Michel Pfeffer, Pascal Hébraud

2014-03-28 Paper

DOI: 10.1039/C4CP00726C

You might also like

Compound Q&A

What is the market or research trend for N-(4-Methoxybenzyl)-2-pyridinamine (CAS: 52818-63-0)?

N-(4-Methoxybenzyl)-2-pyridinamine (CAS: 52818-63-0) is increasingly being used ...

52818-63-0N-(4-Methoxybenzyl)-...
Compound Q&A

What precautions should be taken when handling Ethyl 4-(2-chlorophenyl)-1,3-thiazole-2-carboxylate (CAS: 1050507-06-6)?

When handling Ethyl 4-(2-chlorophenyl)-1,3-thiazole-2-carboxylate, appropriate p...

1050507-06-6Ethyl 4-(2-chlorophe...
Compound Q&A

What regulatory guidelines apply to diethyldiselane (CAS: 628-39-7)?

Diethyldiselane (CAS: 628-39-7) is classified under the Globally Harmonized Syst...

628-39-7Diethyldiselane
Compound Q&A

What is the market or research trend for oxocopper (CAS: 12053-18-8)?

The market for oxocopper (CAS: 12053-18-8) is primarily driven by its use in cat...

12053-18-8oxocopper; oxo-(oxoc...
Compound Q&A

What is the market or research trend for 5-{[(2-Methyl-2-propanyl)oxy]carbonyl}-5-azaspiro[2.4]heptane-7-carboxylic acid?

The market for 5-{[(2-Methyl-2-propanyl)oxy]carbonyl}-5-azaspiro[2.4]heptane-7-c...

1268519-54-55-{[(2-Methyl-2-prop...
Compound Q&A

What is 2-(1-Pyrrolidinyl)-4-pyridinamine (CAS: 35981-63-6)?

2-(1-Pyrrolidinyl)-4-pyridinamine is a chemical compound with the CAS number 359...

35981-63-62-(1-Pyrrolidinyl)-4...
Compound Q&A

What are the physical and chemical properties of 2-(3-Pyridinyl)-1-azabicyclo[2.2.2]octane (CAS: 91556-75-1)?

2-(3-Pyridinyl)-1-azabicyclo[2.2.2]octane (CAS: 91556-75-1) is a crystalline sol...

91556-75-12-(3-Pyridinyl)-1-az...
Compound Q&A

How is (S)-Alpha-allyl-proline hydrochloride (CAS: 129704-91-2) typically synthesized?

(S)-Alpha-allyl-proline hydrochloride is usually synthesized via a Wittig reacti...

129704-91-2(S)-Alpha-allyl-prol...
Compound Q&A

What is 3-Methyl-1,2-oxazole-5-carboxylic acid (CAS: 4857-42-5)?

3-Methyl-1,2-oxazole-5-carboxylic acid (CAS: 4857-42-5) is an organic compound w...

4857-42-53-Methyl-1,2-oxazole...
Compound Q&A

How is Lys-SMCC-DM1 (CAS: 1281816-04-3) typically synthesized?

Lys-SMCC-DM1 is synthesized via a multi-step process involving the coupling of S...

1281816-04-3Lys-SMCC-DM1

Source Journal

Chemical Communications

Chemical Communications
CiteScore: 8.6
Self-citation Rate: 4.7%
Articles per Year: 2458

ChemComm publishes urgent research which is of outstanding significance and interest to experts in the field, while also appealing to the journal’s broad chemistry readership. Our communication format is ideally suited to short, urgent studies that are of such importance that they require accelerated publication. Our scope covers all topics in chemistry, and research at the interface of chemistry and other disciplines (such as materials science, nanoscience, physics, engineering and biology) where there is a significant novelty in the chemistry aspects. Major topic areas covered include: Analytical Chemistry Catalysis Chemical Biology and medicinal chemistry Computational Chemistry and Machine Learning Energy and sustainable chemistry Environmental Chemistry Green Chemistry Inorganic Chemistry Materials Chemistry Nanoscience Organic Chemistry Physical Chemistry Polymer Chemistry Supramolecular Chemistry

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.