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Author:Heikinheimo, Annakaisa
Title:Studies towards the total synthesis of majucin
Tutkimuksia kohti majusiinin kokonaissynteesiä
Publication type:Master's thesis
Publication year:2012
Pages:42 + 4      Language:   eng
Department/School:Kemian laitos
Main subject:Orgaaninen kemia   (Kem-4)
Supervisor:Koskinen, Ari
Instructor:Gomes, José ; Koskinen, Ari
OEVS:
Electronic archive copy is available via Aalto Thesis Database.
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Location:P1 Ark Aalto     | Archive
Keywords:majucin
total synthesis
seco-prezizaane
sesquiterpene
Illicium
majusiini
kokonaissynteesi
seskviterpeeni
Illicium
dementia
Abstract (eng): An increasing health problem in our society is caused by neurodegenerative diseases and injuries, such as Alzheimer's disease.
However, a cure for these diseases is yet to be found.
Many of the seco-prezizaane-type sesquiterpenes from Illicium species have been shown to increase neurite outgrowth and are thus seen as promising targets for lead discovery.
These neurotrophically active molecules include several of the majucin-type.
However, in order for extensive SAR-studies to be carried out on this class of molecules, efficient synthetic methods are needed.

In this master's thesis, synthetic efforts directed towards the total synthesis of majucin are described.
Synthetic methods towards majucin developed earlier by the Gademann group were used for the first twelve steps, starting with the natural product (+)-pulegone.
In this work, four further steps were developed, giving an enantiomerically pure intermediate in 16 steps and 1.3% overall yield.
With this sequence, a particular synthetic challenge that has been faced during the previous efforts could be overcome.

It should be possible to complete the total synthesis in further eight steps.
Further optimization of the developed steps should also be possible and is needed.
With majucin in hand, several of its derivatives could be synthesized in a few steps.
The developed synthetic methods can also be applied in the preparation of other majucin-type natural products.
Abstract (fin): Neurodegeneratiiviset sairaudet ja vauriot, kuten Alzheimerin tauti, ovat yhteiskunnassamme kasvava terveysongelma.
Parannuskeinoa näihin sairauksiin ei kuitenkaan vielä ole.
Monen Illicium-lajin kasveista löydetyn seskviterpeenin on havaittu edistävän aivosolujen kasvua, ja niitä pidetään siksi lupaavina kohteina johtomolekyylien etsinnässä.
Näihin neurotrofisiin molekyyleihin kuuluu myös useita majusiinin tyyppisiä yhdisteitä.
Tehokkaita synteettisiä menetelmiä kuitenkin tarvitaan ennen kuin rakenneaktiivisuus-vuorovaikutusten kattava selvittäminen on mahdollista.

Tässä diplomityössä kuvataan majusiinin kokonaissynteesiin tähtääviä synteettisiä tutkimuksia.
Prof.
Karl Gademannin tutkimusryhmässä majusiinin syntetisoimiseksi kehitettyjä menetelmiä käytettiin ensimmäisissä 12 reaktiovaiheessa, alkaen luonnossa esiintyvästä (+)-pulegonista.
Tässä työssä kuvataan neljän seuraavan vaiheen kehitys.
Enantiomeerisesti puhdas välituote syntetisoitiin yhteensä 16 vaiheessa 1,3 % saannolla.
Näillä neljällä vaiheella voitettiin eräs aiemmin kohdattu erityinen synteettinen haaste.

Majusiini pitäisi olla mahdollista syntetisoida seuraavissa kahdeksassa vaiheessa.
Myös tässä työssä kehitettyjen vaiheiden optimointi on tarpeen.
Useita majusiinin johdannaisia tulisi voida syntetisoida majusiinista muutamassa vaiheessa.
Lisäksi kehitettyjä synteettisiä menetelmiä voitaisiin käyttää muiden majusiinin tyyppisten luonnonaineiden syntetisoimiseen.
ED:2013-01-09
INSSI record number: 45779
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