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Synthesis of novel adamantyl and homoadamantyl substituted β-hydroxybutyric acids


Matković, Marija; Vukelić, Stella; Cirimotić, Ružica; Kragol, Goran; Molčanov, Krešimir; Mlinarić-Majerski, Kata
Synthesis of novel adamantyl and homoadamantyl substituted β-hydroxybutyric acids // Molecular diversity, 17 (2013), 4; 817-826 doi:10.1007/s11030-013-9481-7 (međunarodna recenzija, članak, znanstveni)


Naslov
Synthesis of novel adamantyl and homoadamantyl substituted β-hydroxybutyric acids

Autori
Matković, Marija ; Vukelić, Stella ; Cirimotić, Ružica ; Kragol, Goran ; Molčanov, Krešimir ; Mlinarić-Majerski, Kata

Izvornik
Molecular diversity (1381-1991) 17 (2013), 4; 817-826

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Adamantyl; β-keto ester; β-hydroxybutyric acid; homoadamantyl; hydroxy acids; rearrangement

Sažetak
Several new adamantyl and homoadamantyl substituted β-hydroxybutyric acids, 2-[2-(1-adamantyl)ethyl]-3-hydroxybutyric acid (2), 2-(3-homoadamantyl)-3-hydroxybutyric acid (3) and 2-(1-homoadamantyl)-3-hydroxybutyric acid (4), analogues of the 2-(1-adamantyl)-3-hydroxybutyric acid (1), have been prepared as mixtures of diastereoisomers using selective reduction of corresponding β-keto esters or aldol condensation of the corresponding carboxylic acid and acetaldehyde. The rearrangement of adamantylmethyl and 3-homoadamantyl groups provided entry to both 3-homoadamantyl and 1-homoadamantyl substituted hydroxy acids 3 and 4, respectively. The relative configurations of diastereoisomers 3 and 4 have been determined by NMR spectroscopy comparing the values of coupling constants. Adamantyl substituted β-hydroxybutyric acid 2 has also been prepared in enantiomerically pure form by Evan’s asymmetric synthesis and the absolute configuration has been determined by X-ray crystallography. Contrary to the long-chain acid 2, the attempt to prepare short-chain hydroxy acids 1 and 4 by the same method failed indicating pronounced sensitivity of the used method to the vicinity of the bulky cage group.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
098-0982933-2911 - Kavezasti spojevi: ugradbene jedinice u molekularnim sustavima (Kata Majerski, )

Ustanove
Institut "Ruđer Bošković", Zagreb

Citiraj ovu publikaciju

Matković, Marija; Vukelić, Stella; Cirimotić, Ružica; Kragol, Goran; Molčanov, Krešimir; Mlinarić-Majerski, Kata
Synthesis of novel adamantyl and homoadamantyl substituted β-hydroxybutyric acids // Molecular diversity, 17 (2013), 4; 817-826 doi:10.1007/s11030-013-9481-7 (međunarodna recenzija, članak, znanstveni)
Matković, M., Vukelić, S., Cirimotić, R., Kragol, G., Molčanov, K. & Mlinarić-Majerski, K. (2013) Synthesis of novel adamantyl and homoadamantyl substituted β-hydroxybutyric acids. Molecular diversity, 17 (4), 817-826 doi:10.1007/s11030-013-9481-7.
@article{article, year = {2013}, pages = {817-826}, DOI = {10.1007/s11030-013-9481-7}, keywords = {adamantyl, β-keto ester, β-hydroxybutyric acid, homoadamantyl, hydroxy acids, rearrangement}, journal = {Molecular diversity}, doi = {10.1007/s11030-013-9481-7}, volume = {17}, number = {4}, issn = {1381-1991}, title = {Synthesis of novel adamantyl and homoadamantyl substituted β-hydroxybutyric acids}, keyword = {adamantyl, β-keto ester, β-hydroxybutyric acid, homoadamantyl, hydroxy acids, rearrangement} }

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus
  • MEDLINE


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