Ni-Pd Catalyzed Cyclization of Sulfanyl 1,6-Diynes: Synthesis of 1'-Homonucleoside Analogues

被引：9

作者：

Kobayashi, Yuka ^{[1
]}

Tanahashi, Rena ^{[1
]}

Yamaguchi, Yui ^{[3
]}

Hatae, Noriyuki ^{[2
]}

Kobayashi, Masanori ^{[4
]}

Ueno, Yoshihito ^{[5
]}

Yoshimatsu, Mitsuhiro ^{[1
,3
]}

机构：

[1] Gifu Univ, Dept Chem, Fac Educ, Yanagido 1-1, Gifu 5011193, Japan

[2] Hlth Sci Univ Hokkaido, Sch Pharmaceut Sci, Ishikari, Hokkaido 0610293, Japan

[3] Gifu Univ, Fac Appl Biol Sci, Lab Vet Microbiol, Yanagido 1-1, Gifu 5011193, Japan

[4] Gifu Univ, Dept Res Promot, Org Res & Community Dev, Yanagido 1-1, Gifu 5011193, Japan

[5] Gifu Univ, United Grad Sch Agr Sci, Dept Smart Mat Sci, Yanagido 1-1, Gifu 5011193, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 05期

关键词：

TRANSITION-STATE ANALOG; PROTOZOAN NUCLEOSIDE HYDROLASES; ANTIVIRAL DRUGS; NUCLEIC-ACID; STEREOSELECTIVE-SYNTHESIS; REVERSE-TRANSCRIPTASE; CROSS-METATHESIS; IN-VITRO; DERIVATIVES; INHIBITORS;

D O I：

10.1021/acs.joc.6b02841

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 N-3-benzoylthymine, N-4,N-4-bis(Boc)cytosine, N-3-benzoyluracil and N-6,N-6-bis(Boc)adenine exclusively afforded the pyrrolylmethyl and furylmethyl nucleotides in good yields. Deprotection of nucleobases was completed by treatment with adds or bases. Furthermore, the reactions of pyrroles and furans with nucleophiles such as alkoxides and amines underwent detosylation arylaminomethyl-pyrroles and furans in good yields. and conversion to the alkoxymethyl- and arylaminomethyl-pyrroles and furans in good yields.

引用

页码：2436 / 2449

页数：14

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