TY - JOUR
T1 - Adamantyl-β-butyrolactones
T2 - Synthesis and ring-opening reactions
AU - Matković, Marija
AU - Molčanov, Krešimir
AU - Glaser, Robert
AU - Mlinarić-Majerski, Kata
N1 - Funding Information:
This research was supported by the Ministry of Science, Education and Sports of the Republic of Croatia (Grant no. 098-0982933-2911 ) and HAZU (Grant awarded to M. Matković). Authors would like to thank Dr. M. Cindrić for MS-analysis by tandem mass spectroscopy.
PY - 2012/10/21
Y1 - 2012/10/21
N2 - 2-(1-Adamantyl)-β-butyrolactones 3a and 3b were synthesized using very common peptide coupling reagents under mild conditions and their ring-opening reactions were then studied. These novel lactones showed pronounced stability and were resistant to cleavage upon acidic water extraction and column chromatographic purification. The adamantane moiety plays an important function in lowering the lactone reactivity by protecting the electrophilic sites on the four membered ring via steric hindrance. However under certain conditions, both O-C(carbonyl) and O-C(alkyl) bond-cleavage ring-opening reactions were observed. Bond-cleavage at physiological temperature makes these novel lactones especially noteworthy. Novel adamantyl-β-butyrolactones have a potential to act as biomembrane soluble amphiphiles that might exhibit a combination of stability and biological activity with the latter hopefully predominating.
AB - 2-(1-Adamantyl)-β-butyrolactones 3a and 3b were synthesized using very common peptide coupling reagents under mild conditions and their ring-opening reactions were then studied. These novel lactones showed pronounced stability and were resistant to cleavage upon acidic water extraction and column chromatographic purification. The adamantane moiety plays an important function in lowering the lactone reactivity by protecting the electrophilic sites on the four membered ring via steric hindrance. However under certain conditions, both O-C(carbonyl) and O-C(alkyl) bond-cleavage ring-opening reactions were observed. Bond-cleavage at physiological temperature makes these novel lactones especially noteworthy. Novel adamantyl-β-butyrolactones have a potential to act as biomembrane soluble amphiphiles that might exhibit a combination of stability and biological activity with the latter hopefully predominating.
KW - Adamantyl-β-butyrolactones
KW - C(alkyl)-O(acyl) bond-cleavage
KW - C(carbonyl)-O(acyl) bond-cleavage
KW - Lactonization
KW - β-Lactones
UR - http://www.scopus.com/inward/record.url?scp=84865799274&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2012.07.102
DO - 10.1016/j.tet.2012.07.102
M3 - Article
AN - SCOPUS:84865799274
SN - 0040-4020
VL - 68
SP - 8795
EP - 8804
JO - Tetrahedron
JF - Tetrahedron
IS - 42
ER -