Synthesis of simple 2'-alkoxymethyl substituted klavuzon derivatives
tarafından
 
Çetinkaya, Hakkı, author.

Başlık
Synthesis of simple 2'-alkoxymethyl substituted klavuzon derivatives

Yazar
Çetinkaya, Hakkı, author.

Yazar Ek Girişi
Çetinkaya, Hakkı, author.

Fiziksel Tanımlama
xiv, 122 leaves:+ 1 computer laser optical disc.

Özet
α,β-Unsaturated δ-lactones are the members of lactones, which are cyclic esters. They are quite valuable compounds because of their Michael acceptor property at unsaturated carbonyl functional group. It is believed that soft nucleophilic parts of the enzymes react with the β-carbon of lactone and form a covalent bond. If that is occurred at the active site of an enzyme, its activity is inhibited irreversibly. (R)-goniothalamin is a α,β-unsaturated lactone and it was shown that it has a selective cytotoxic activity over cancer cells. It is less cytotoxic in healthy cells. Later, Kasaplar and coworkers synthesized the klavuzon derivatives, which can be considered as the close relatives of goniothalamins. In this study novel derivatives of simple 2’-alkoxymethyl substituted klavuzon derivatives were synthesized. For this purpose, we started with 2-methyl-1-naphtoic acid, which can be transferred to ethyl 2-methyl-1-naphtoate by reacting with iodoethane under basic condition. Next, formed ester reacted with Br2 molecules generated in situ by NaBrO3 and NaHSO3. Then formed ethyl 2-(bromomethyl)-1-naphtoate reacted with various alcohols under basic conditions to form ethyl-2-alkoxymethyl-1-naphtoate. These esters are coverted to the target klavuzon products in five steps that are reduction with LiAlH4, oxidation with PCC, addition of allylmagnesium bromide, acrylate ester formation and ring closing metathesis reactions.

Konu Başlığı
Chemistry, Organic.
 
Lactones.
 
Bioorganic chemistry.

Yazar Ek Girişi
Çağır, Ali,

Tüzel Kişi Ek Girişi
İzmir Institute of Technology. Chemistry.

Tek Biçim Eser Adı
Thesis (Master)--İzmir Institute of Technology:Chemistry.
 
İzmir Institute of Technology:Chemistry--Thesis (Master).

Elektronik Erişim
Access to Electronic Versiyon.


LibraryMateryal TürüDemirbaş NumarasıYer Numarası
IYTE LibraryTezT001660QD305.A2 C42 2017