A Novel, One-Pot Ring Expansion of Cyclobutanones. Syntheses of Carbovir and Aristeromycin

A Novel, One-Pot Ring Expansion of Cyclobutanones. Syntheses of Carbovir and Aristeromycin

A novel, one-pot ring-expansion procedure was developed using Me3S(O)I, NaH, and Sc(OTf)3. The scope and limitations were briefly examined, and a tentative mechanism was proposed. Application of the methodology to known cyclobutanone 1 provided the corresponding cyclopentanone, which was successfull...

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Veröffentlicht in:Journal of organic chemistry 2000-03, Vol.65 (6), p.1865-1872
Hauptverfasser: Brown, Brian, Hegedus, Louis S
Format: Artikel
Sprache:eng
Schlagworte:
Adenosine - analogs & derivatives
Adenosine - chemical synthesis
AIDS/HIV
Anti-HIV Agents - chemical synthesis
Butanones - chemical synthesis
Dideoxynucleosides - chemical synthesis
Stereoisomerism
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Zusammenfassung:A novel, one-pot ring-expansion procedure was developed using Me3S(O)I, NaH, and Sc(OTf)3. The scope and limitations were briefly examined, and a tentative mechanism was proposed. Application of the methodology to known cyclobutanone 1 provided the corresponding cyclopentanone, which was successfully advanced to (+)-carbovir and (+)-aristeromycin.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo9919759