261511-22-2Relevant academic research and scientific papers
Synthesis of 2′,3′-modified carbocyclic L -nucleoside analogues
Jessel, Soenke,Meier, Chris
, p. 1702 - 1713 (2011/05/04)
New divergent approaches to 2′,3′-modified carbocyclic L-nucleoside analogues starting from enantiomerically pure (1R,2S)- or (1S,2R)-2-(benzyloxymethyl)cyclopent-3-enol are described. In the key step, stereochemically pure cyclopentanols were condensed with N3-protected thymine through a modified Mitsunobu protocol. Moreover, several routes to different cyclopentanol derivatives, to prepare carbocyclic L-2′,3′-didehydro- 2′,3′-dideoxynucleosides (L-d4N), L-2′,3′- dideoxynucleosides (L-ddN), and L-ribonucleosides are reported. Copyright
A Novel, One-Pot Ring Expansion of Cyclobutanones. Syntheses of Carbovir and Aristeromycin
Brown, Brian,Hegedus, Louis S.
, p. 1865 - 1872 (2007/10/03)
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.
Mechanism and applications of lithium amide-induced asymmetric rearrangements of 4-substituted and 4,4-disubstituted cyclopentene oxides to cyclopentenols
Hodgson, David M.,Gibbs, Andrew R.,Drew, Michael G. B.
, p. 3579 - 3590 (2007/10/03)
The preparation and lithium amide-induced rearrangements of 1,2-dideuterated 4-substituted cyclopentene oxides 11 and 19 are described, providing insight into the deprotonation mechanisms operating in such systems. Highly enantioselective syntheses of 4-substituted cis-4-hydroxymethylcyclopent-2-en-1-ols 32a-c are described. Also described are asymmetric syntheses of prostaglandin precursor 40 and (+)-iridomyrmecin (48) via highly enantioselective rearrangement of the epoxide 3 and subsequent Ireland-Claisen rearrangement. The Royal Society of Chemistry 1999.
An Enantioselective Epoxide Rearrangement - Claisen Rearrangement Approach to Prostaglandins and (+)-Iridomyrmecin
Hodgson, David M.,Gibbs, Andrew R.
, p. 657 - 658 (2007/10/03)
The asymmetric syntheses of prostaglandin precursor 8 and (+)iridomyrmecin (12) via highly enantioselective rearrangement of the epoxide 1 and subsequent Ireland-Claisen rearrangement are described.
