Ni-Pd Catalyzed Cyclization of Sulfanyl 1,6-Diynes: Synthesis of 1'-Homonucleoside Analogues.
The Ni-Pd catalyzed addition-cyclization of sulfanyl 1,6-diynes 2-9 with nucleobases is described. The reactions of N-tethered 1,6-diynes with N3-benzoylthymine, N4,N4-bis(Boc)cytosine, N3-benzoyluracil and N6,N6-bis(Boc)adenine exclusively afforded the pyrrolylmethyl and furylmethyl nucleotides in good yields. Deprotection of nucleobases was completed by treatment with acids or bases. Furthermore, the reactions of pyrroles and furans with nucleophiles such as alkoxides and amines underwent detosylation and conversion to the alkoxymethyl- and arylaminomethyl-pyrroles and furans in good yields.
Department of Chemistry, Faculty of Education, Gifu University , Yanagido 1-1, Gifu 501-1193, Japan.
Yuka
Y
Kobayashi
Department of Chemistry, Faculty of Education, Gifu University , Yanagido 1-1, Gifu 501-1193, Japan.
Rena
R
Tanahashi
Laboratory of Veterinary Microbiology, Faculty of Applied Biological Sciences, Gifu University , Yanagido 1-1, Gifu 501-1193, Japan.
Yui
Y
Yamaguchi
School of Pharmaceutical Sciences, Health Science University of Hokkaido , Ishikari-Tobetsu, Hokkaido 061-0293, Japan.
Noriyuki
N
Hatae
Organization for Research and Community Development, Department of Research Promotion, Gifu University , Yanagido 1-1, Gifu 501-1193, Japan.
Masanori
M
Kobayashi
Department of Smart Material Science, The United Graduate School of Agricultural Science, Gifu University , Yanagido 1-1, Gifu 501-1193, Japan.
Yoshihito
Y
Ueno
Department of Chemistry, Faculty of Education, Gifu University , Yanagido 1-1, Gifu 501-1193, Japan.|Laboratory of Veterinary Microbiology, Faculty of Applied Biological Sciences, Gifu University , Yanagido 1-1, Gifu 501-1193, Japan.
Mitsuhiro
0000-0001-6791-4040
M
Yoshimatsu