NDLI: A Straightforward Total Synthesis of (−)-Chaetominine

Please wait, while we are loading the content...

Year: 2017 Volume: 23

Year: 2016 Volume: 22

Year: 2015 Volume: 21

Year: 2014 Volume: 20

Year: 2013 Volume: 19

Year: 2012 Volume: 18

Year: 2011 Volume: 17

Year: 2010 Volume: 16

Year: 2009 Volume: 15

Year: 2009 Volume: 15 Issue: 48

Year: 2009 Volume: 15 Issue: 47

Year: 2009 Volume: 15 Issue: 46

Year: 2009 Volume: 15 Issue: 45

Year: 2009 Volume: 15 Issue: 44

Year: 2009 Volume: 15 Issue: 43

Year: 2009 Volume: 15 Issue: 42

Year: 2009 Volume: 15 Issue: 41

Year: 2009 Volume: 15 Issue: 40

Year: 2009 Volume: 15 Issue: 39

Year: 2009 Volume: 15 Issue: 38

Year: 2009 Volume: 15 Issue: 37

Year: 2009 Volume: 15 Issue: 36

Year: 2009 Volume: 15 Issue: 35

Year: 2009 Volume: 15 Issue: 34

Year: 2009 Volume: 15 Issue: 33

Year: 2009 Volume: 15 Issue: 32

Asymmetric iminium ion catalysis with a novel bifunctional primary amine thiourea: controlling adjacent quaternary and tertiary stereocenters.

Mechanistic Study of the Palladium–Phenanthroline Catalyzed Carbonylation of Nitroarenes and Amines: Palladium–Carbonyl Intermediates and Bifunctional Effects

Adducts between Dansylated Poly(propylene amine) Dendrimers and Anthracene Clips Mediated by $Zn^{II}$ Ions: Highly Efficient Photoinduced Energy Transfer

Determination of the Catalytic Pathway of a Manganese Arginase Enzyme Through Density Functional Investigation

Preparation and Characterisation of a New Inclusion Compound of Cucurbit[8]uril with a Nitroxide Radical

Diastereoselective, One-Pot Synthesis of Polyfunctionalized Bicyclo[3.3.1]nonanes by an Anionic Domino Process

Nanofibers from Oxazolidi-2-one Containing Hybrid Foldamers: What is the Right Molecular Size?

Michael Additions versus Cycloaddition Condensations with Ethyl Nitroacetate and Electron-Deficient Olefins

Catalytic Asymmetric Baeyer–Villiger Oxidation in Water by Using $Pt^{II}$ Catalysts and Hydrogen Peroxide: Supramolecular Control of Enantioselectivity

Predicting the NMR Spectra of Paramagnetic Molecules by DFT: Application to Organic Free Radicals and Transition-Metal Complexes

Guanosine Hydrogen-Bonded Scaffolds: A New Way to Control the Bottom-Up Realisation of Well-Defined Nanoarchitectures

Palladium/Norbornene-Catalyzed Synthesis of Heteroatom-Containing o-Teraryls from Aryl Iodides and Heteroarenes through Double CH Activation in Sequence

Bifunctional Catalysis by Natural Cinchona Alkaloids: A Mechanism Explained

Polyamine Receptors Containing Dipyridine or Phenanthroline Units: Clues for the Design of Fluorescent Chemosensors for Metal Ions

Diversity-Oriented Synthesis of Morpholine-Containing Molecular Scaffolds

One Hundred Years of the Italian Chemical Society—One Hundred Years of Chemistry

The Birth of a Chemical Society

From Azides to Nitrogen-Centered Radicals: Applications of Azide Radical Chemistry to Organic Synthesis

Stanislao Cannizzaro and the Development of Chemistry in Palermo from 1862 to 1871

Release of Toxic $Gd^{3+}$ Ions to Tumour Cells by $Vitamin B_{12}$ Bioconjugates

A Study of the Influence of Ionic Liquids Properties on the Kemp Elimination Reaction

A Straightforward Total Synthesis of (−)-Chaetominine

Fifty Years of Chemical Research at Farmitalia

The Role of Building-Block Metrics in the Halogen-Bonding-Driven Self-Assembly of Calixarenes, Inorganic Salts and Diiodoperfluoroalkanes

Stereospecific Synthesis of $β^{3}-Amino$ Acid Derivatives from Propargylic Alcohols: Efficient Solution-Phase Synthesis of Oligopeptides without Coupling Agents

Magnetism in Nanoparticles: Beyond the Effect of Particle Size

Is the Backbone Conformation of $C^{α}-Methyl$ Proline Restricted to a Single Region?

Stereocontrolled Cyclic Nitrone Cycloaddition Strategy for the Synthesis of Pyrrolizidine and Indolizidine Alkaloids

Iron-Substituted Polyoxotungstates as Inorganic Synzymes: Evidence for a Biomimetic Pathway in the Catalytic Oxygenation of Catechols

Electrochemical Characterisation of 6-Iodomaltose, 6′-Iodomaltose and 6-Iodomaltotriose on a Silver Cathode and Their One-Pot Electrochemical Dimerisation to New Mixed O/C Maltotetraose and Maltohexaose Mimics

Regio- and Stereoselectivity in the Decatungstate Photocatalyzed Alkylation of Alkenes by Alkylcyclohexanes

Characterisation of the MMP-12–Elastin Adduct

Oxygen-Atom Transfer by a Naked Manganese(V)–Oxo–Porphyrin Complex Reveals Axial Ligand Effect

On the Dichotomic Reactivity of Lithiated Styrene Oxide: A Computational and Multinuclear Magnetic Resonance Investigation

Year: 2009 Volume: 15 Issue: 31

Year: 2009 Volume: 15 Issue: 30

Year: 2009 Volume: 15 Issue: 29

Year: 2009 Volume: 15 Issue: 28

Year: 2009 Volume: 15 Issue: 27

Year: 2009 Volume: 15 Issue: 26

Year: 2009 Volume: 15 Issue: 25

Year: 2009 Volume: 15 Issue: 24

Year: 2009 Volume: 15 Issue: 23

Year: 2009 Volume: 15 Issue: 22

Year: 2009 Volume: 15 Issue: 21

Year: 2009 Volume: 15 Issue: 20

Year: 2009 Volume: 15 Issue: 19

Year: 2009 Volume: 15 Issue: 18

Year: 2009 Volume: 15 Issue: 17

Year: 2009 Volume: 15 Issue: 16

Year: 2009 Volume: 15 Issue: 15

Year: 2009 Volume: 15 Issue: 14

Year: 2009 Volume: 15 Issue: 13

Year: 2009 Volume: 15 Issue: 12

Year: 2009 Volume: 15 Issue: 11

Year: 2009 Volume: 15 Issue: 10

Year: 2009 Volume: 15 Issue: 9

Year: 2009 Volume: 15 Issue: 8

Year: 2009 Volume: 15 Issue: 7

Year: 2009 Volume: 15 Issue: 6

Year: 2009 Volume: 15 Issue: 5

Year: 2009 Volume: 15 Issue: 4

Year: 2009 Volume: 15 Issue: 3

Year: 2009 Volume: 15 Issue: 2

Year: 2009 Volume: 15 Issue: 1

Year: 2008 Volume: 14

Year: 2007 Volume: 13

Year: 2006 Volume: 12

Year: 2005 Volume: 11

Year: 1997 Volume: 3

A Straightforward Total Synthesis of (−)-Chaetominine

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Papeo, Gianluca Quartieri, Francesca Malgesini, Beatrice Forte, Barbara Gennari, Cesare Borghi, Daniela
Description	Author Affiliation: Malgesini B ( Chemical Core Technologies, Nerviano Medical Sciences, Viale Pasteur 10, 20014 Nerviano (MI), Italy.)
Abstract	A total synthesis of the tripeptide alkaloid (−)-chaetominine (1) was achieved in 9.3 % overall yield starting from commercially available D-tryptophan methyl ester, based on a short and straightforward (nine steps) sequence. The early stage introduction (first step) of the quinazolinone moiety and the late stage introduction (penultimate step) of the hydroxy group allowed a synthetic strategy devoid of protective groups. The key step of the process is the a–c tricyclic ring construction via an unprecedented NCS-mediated N-acyl cyclization on an indole ring to give tetrahydro-1H-pyrido[2,3-b]indole 11. In the penultimate step, oxidation of the tetracyclic intermediate 14 with oxaziridine 15 gave only one of the four possible diastereoisomers, the cis-diastereoisomer 16 resulting from the attack of the oxaziridine to the double bond face opposite to the c–d ring substituents. In the last step, the complete stereocontrol of the $Et_{3}SiH/TFA$ reduction of compound 16, probably involving a N-acyliminium ion, can be attributed to ring constrain, which forces the b–c ring junction in the more stable cis-orientation. (−)-Chaetominine (1) showed a negligible inhibitory activity on several cancer cell lines.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	32
Volume Number	15
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2009-08-10
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Indole Alkaloids Chemical Synthesis Drug Screening Assays, Antitumor Chemistry Pharmacology Molecular Structure Peptides, Cyclic Quinazolines Stereoisomerism Research Support, Non-U.S. Gov't
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

Central Library (ISO-9001:2015 Certified)
Indian Institute of Technology Kharagpur
Kharagpur, West Bengal, India | PIN - 721302

See location in the Map
03222 282435
Mail: support@ndl.gov.in

Sl.	Authority	Responsibilities	Communication Details
1	Ministry of Education (GoI), Department of Higher Education	Sanctioning Authority	https://www.education.gov.in/ict-initiatives
2	Indian Institute of Technology Kharagpur	Host Institute of the Project: The host institute of the project is responsible for providing infrastructure support and hosting the project	https://www.iitkgp.ac.in
3	National Digital Library of India Office, Indian Institute of Technology Kharagpur	The administrative and infrastructural headquarters of the project	Dr. B. Sutradhar bsutra@ndl.gov.in
4	Project PI / Joint PI	Principal Investigator and Joint Principal Investigators of the project	Dr. B. Sutradhar bsutra@ndl.gov.in Prof. Saswat Chakrabarti will be added soon
5	Website/Portal (Helpdesk)	Queries regarding NDLI and its services	support@ndl.gov.in
6	Contents and Copyright Issues	Queries related to content curation and copyright issues	content@ndl.gov.in
7	National Digital Library of India Club (NDLI Club)	Queries related to NDLI Club formation, support, user awareness program, seminar/symposium, collaboration, social media, promotion, and outreach	clubsupport@ndl.gov.in
8	Digital Preservation Centre (DPC)	Assistance with digitizing and archiving copyright-free printed books	dpc@ndl.gov.in
9	IDR Setup or Support	Queries related to establishment and support of Institutional Digital Repository (IDR) and IDR workshops	idr@ndl.gov.in