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- W1976315390 abstract "New dienophiles, dimethyl acetoxymethylenemalonate and its analogues, have been synthesized. These dienophiles reacted with cyclopentadiene to give Diels-Alder adducts, which served as versatile synthetic precursors for carbocyclic C-nucleosides. The method has the following three characteristics: (1) the C-C bond in the adduct originated from the dienophile can be cleaved stereoselectively by the reductive retrograde aldol (RRA) reaction, (2) the CC bond in the adduct serves as a latent functionality of 2′- and 3′- positions of the nucleoside, and (3) the malonate unit can be transformed to a variety of heterocycles. The high pressure mediated Diels-Alder reaction of furan with the same dienophiles also gave the cycloadducts, which served as synthons for C-nucleosides. Use of chiral dienophiles, such as di-1-menthyl acetoxymethylenemalonate, for the above Diels-Alder reactions has offered a new route to the enantioselective synthesis of C-nucleosides and their carbocyclic analogues. Essentially the same methodology has also been applied to the synthesis of carbocyclic nucleosides from 2-azabicyclo[2.2.1]hept-5-en-3-one, in which a reductive amido bond cleavage reaction similar to (1) is involved. Synthesis of carbocyclic oxetanocin and its analogues is also described." @default.
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- W1976315390 date "1991-01-01" @default.
- W1976315390 modified "2023-10-05" @default.
- W1976315390 title "A New Method for the Stereoselective Synthesis of Nucleosides by Means of Sodium Borohydride Mediated Reductive C-C or C-N Bond Cleavage Reaction" @default.
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- W1976315390 doi "https://doi.org/10.1002/ijch.199100029" @default.
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