A novel, one-pot ring expansion of cyclobutanones. Syntheses of carbovir and aristeromycin
B Brown, LS Hegedus
Index: Brown, Brian; Hegedus, Louis S. Journal of Organic Chemistry, 2000 , vol. 65, # 6 p. 1865 - 1872
Full Text: HTML
Citation Number: 62
Abstract
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.
Related Articles:
[McGuigan, Christopher; Hassan-Abdallah, Alshaimaa; Srinivasan, Sheila; Wang, Yikang; Siddiqui, Adam; Daluge, Susan M.; Gudmundsson, Kristjan S.; Zhou, Huiqiang; McLean, Ed W.; Peckham, Jennifer P.; Burnette, Thimysta C.; Marr, Harry; Hazen, Richard; Condreay, Lynn D.; Johnson, Lance; Balzarini, Jan Journal of Medicinal Chemistry, 2006 , vol. 49, # 24 p. 7215 - 7226]
Asymmetric synthesis and anti-HIV activity of L-carbocyclic 2′, 3′-didehydro-2′, 3′-dideoxyadenosine
[Wang, Peiyuan; Schinazi, Raymond F.; Chu, Chung K. Bioorganic and Medicinal Chemistry Letters, 1998 , vol. 8, # 13 p. 1585 - 1588]
Asymmetric synthesis and anti-HIV activity of L-carbocyclic 2′, 3′-didehydro-2′, 3′-dideoxyadenosine
[Wang, Peiyuan; Schinazi, Raymond F.; Chu, Chung K. Bioorganic and Medicinal Chemistry Letters, 1998 , vol. 8, # 13 p. 1585 - 1588]
Asymmetric synthesis and anti-HIV activity of L-carbocyclic 2′, 3′-didehydro-2′, 3′-dideoxyadenosine
[Wang, Peiyuan; Schinazi, Raymond F.; Chu, Chung K. Bioorganic and Medicinal Chemistry Letters, 1998 , vol. 8, # 13 p. 1585 - 1588]
Asymmetric synthesis and anti-HIV activity of L-carbocyclic 2′, 3′-didehydro-2′, 3′-dideoxyadenosine
[Wang, Peiyuan; Schinazi, Raymond F.; Chu, Chung K. Bioorganic and Medicinal Chemistry Letters, 1998 , vol. 8, # 13 p. 1585 - 1588]