search query: @supervisor Jokela, Reija / total: 35
reference: 2 / 35
« previous | next »
Author:Kylmälä, Heli
Title:Microwave-assisted total synthesis of tangutorine
Mikroaaltoavusteinen tangutoriinin kokonaissynteesi
Publication type:Licentiate thesis
Publication year:2013
Pages:viii + 46 s. + liitt. 10      Language:   eng
Department/School:Kemian tekniikan korkeakoulu
Main subject:Orgaaninen kemia   (Kem-4)
Supervisor:Jokela, Reija
Instructor:
Electronic version URL: http://urn.fi/URN:NBN:fi:aalto-201507013633
OEVS:
Electronic archive copy is available via Aalto Thesis Database.
Instructions

Reading digital theses in the closed network of the Aalto University Harald Herlin Learning Centre

In the closed network of Learning Centre you can read digital and digitized theses not available in the open network.

The Learning Centre contact details and opening hours: https://learningcentre.aalto.fi/en/harald-herlin-learning-centre/

You can read theses on the Learning Centre customer computers, which are available on all floors.

Logging on to the customer computers

  • Aalto University staff members log on to the customer computer using the Aalto username and password.
  • Other customers log on using a shared username and password.

Opening a thesis

  • On the desktop of the customer computers, you will find an icon titled:

    Aalto Thesis Database

  • Click on the icon to search for and open the thesis you are looking for from Aaltodoc database. You can find the thesis file by clicking the link on the OEV or OEVS field.

Reading the thesis

  • You can either print the thesis or read it on the customer computer screen.
  • You cannot save the thesis file on a flash drive or email it.
  • You cannot copy text or images from the file.
  • You cannot edit the file.

Printing the thesis

  • You can print the thesis for your personal study or research use.
  • Aalto University students and staff members may print black-and-white prints on the PrintingPoint devices when using the computer with personal Aalto username and password. Color printing is possible using the printer u90203-psc3, which is located near the customer service. Color printing is subject to a charge to Aalto University students and staff members.
  • Other customers can use the printer u90203-psc3. All printing is subject to a charge to non-University members.
Location:P1 Ark Aalto  2360   | Archive
Keywords:indole alkaloid
tangutorine
microwaves
indolialkaloidi
tangutoriini
mikroaallot
Abstract (eng): Indole alkaloids are widely found from the nature.
Many indole alkaloids show physiological activity and they can be used e.g. as anti-inflammatory agents and ß-adrenergic blockers.
Since their isolation is not very profitable and the obtained isolated amounts are relatively small they have to be synthesized.
There are many total syntheses reported for the pharmacologically important indole alkaloids.
Microwave-assisted reactions are in the main focus in this licentiate thesis.
Microwaves are abundantly used in organic syntheses.
Microwaves speed up the reactions by transferring the energy directly to reacting molecules.
Microwave assisted methods have enabled environmentally friendly reactions.
Also solvent free reactions are possible.
Reactions are also reproducible due to temperature and pressure control.

Tangutorine is a biogenetically interesting indole alkaloid because to date it is the only known natural product containing the benz[f]indolo[2,3-a]quinolizidine unit.
It was isolated from Nitraria tangutorum by Duan et al. in 1999.
So far seven total syntheses as well as two formal syntheses and two synthetic approaches of tangutorine have been published.
In this licentiate thesis the first microwave assisted total synthesis of tangutorine containing six steps where three of them were done with microwave irradiation is reported.
In addition to microwave-assisted total synthesis of tangutorine, microwave-assisted monoacetal and -thioacetal protections of symmetrical dialdehydes are reported.
Abstract (fin): Indolialkaloideja esiintyy laajasti luonnossa.
Monilla indolialkaloideilla on todettu fysiologista aktiivisuutta, ja niitä voidaan käyttää esimerkiksi tulehdusten ja ß-adrenergisten reseptorien estäjinä.
Koska indolialkaloidien eristäminen luonnosta ei ole kovin kannattavaa ja eristämisessä saadut määrät ovat pieniä, täytyy ne syntetisoida.
Farmakologisesti tärkeille indolialkaloideille on raportoitu useita kokonaissynteesejä.
Tässä Iisensiaatintyössä pääosassa ovat mikroaaltoavusteiset reaktiot.
Mikroaaltoja käytetään nykyisin paljon orgaanisissa synteeseissä.
Ne nopeuttavat reaktioita siirtämällä energian suoraan reagoiviin molekyyleihin.
Mikroaaltoreaktiot ovat mahdollistaneet ymparist6ystavalliset reaktiot sekä reaktiot ilman liuottimia.
Lisaksi reaktiot ovat toistettavia lamp6tilan ja paineen kontrolloimisen vuoksi.

Tangutoriini on biogeneettisesti kiinnostava indolialkaloidi, koska se on ainoa tähän päivään mennessä löydetty luonnonaine, joka sisältää bents[f]indoli[2,3- a]kinolitsidiiniyksikön.
Duat et al. eristivät tangutoriinin vuonna 1999 Nitraria tangutorum -kasvista.
Tähän mennessä tangutoriinille on julkaistu seitsemän kokonaissynteesiä, kaksi muodollista synteesiä sekä kaksi synteettistä lähestymistapaa.
Tässä lisensiaatintyössä raportoidaan ensimmäinen mikroaaltoavusteinen tangutoriinin kokonaissynteesi, jossa on kuusi vaihetta, joista kolme on tehty käyttäen mikroaaltosäteilytystä.
Tämän kokonaissynteesin lisäksi tässä työssä raportoidaan symmetristen dialdehydien monoasetaali- ja monotioasetaalisuojaukset, mitkä on tehty mikroaaltoavusteisesti.
ED:2014-04-14
INSSI record number: 48884
+ add basket
« previous | next »
INSSI