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

Title
Synthesis of simple 2'-alkoxymethyl substituted klavuzon derivatives

Author
Çetinkaya, Hakkı, author.

Personal Author
Çetinkaya, Hakkı, author.

Physical Description
xiv, 122 leaves:+ 1 computer laser optical disc.

Abstract
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.

Subject Term
Chemistry, Organic.
 
Lactones.
 
Bioorganic chemistry.

Added Author
Çağır, Ali,

Added Corporate Author
İzmir Institute of Technology. Chemistry.

Added Uniform Title
Thesis (Master)--İzmir Institute of Technology:Chemistry.
 
İzmir Institute of Technology:Chemistry--Thesis (Master).

Electronic Access
Access to Electronic Versiyon.


LibraryMaterial TypeItem BarcodeShelf NumberStatus
IYTE LibraryThesisT001660QD305.A2 C42 2017Tez Koleksiyonu
IYTE LibrarySupplementary CD-ROMROM2824QD305.A2 C42 2017 EK.1Tez Koleksiyonu