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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 <b>2</b>–<b>9</b> with nucleobases is
described. The reactions of <i>N</i>-tethered 1,6-diynes
with <i>N</i><sup>3</sup>-benzoylthymine, <i>N</i><sup>4</sup>,<i>N</i><sup>4</sup>-bisÂ(Boc)Âcytosine, <i>N</i><sup>3</sup>-benzoyluracil and <i>N</i><sup>6</sup>,<i>N</i><sup>6</sup>-bisÂ(Boc)Âadenine 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