Tetrahedron Letters p. 5517 - 5520 (1998)
Update date:2022-08-05
Topics:
Haraguchi, Kazuhiro
Hosoe, Motoi
Tanaka, Hiromichi
Tsuruoka, Sayo
Kanmuri, Kazuhiro
Miyasaka, Tadashi
A new stereoselective ring construction for 3,7-anhydrooctofuranosyl nucleoside, which is based on a 6-endo-trig oxyselenation of a conjugate diene, (5'S)-C-(4-phenyl-1,3-butadienyl)uridine, was developed. Because of the appropriate array of functionalities at the 5', 6', and 7'-positions, the cyclization product 14 can be considered to be a versatile synthon for the synthesis of a series of octosyl nucleoside antibiotics. Factors governing the efficiency of this cyclization are also discussed.
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