54483-54-4Relevant academic research and scientific papers
Stereoselective synthesis of α-L-bicarbocyclic nucleosides as potential antiviral drugs
Demaison, Christine,Hourioux, Christophe,Roingeard, Philippe,Agrofoglio, Luigi A.
, p. 9175 - 9178 (1998)
Synthesis of hitherto unknown carbocyclic α-L-isomeric bicyclo[3.1.0]hexyl nucleosides (8-11) is described. The key intermediate 7 was synthesized in seven steps from the known chiral compound 1 through a stereoselective cyclopropanation under Furukawa conditions. Compounds 8-11 were evaluated as anti-HBV agents in HepG2T14 cells.
Enantiomeric synthesis of L- (or 1S,2R,3S,5S)-bicarbocyclic[3.1.0] nucleosides
Agrofoglio, Luigi A.,Demaison, Christine,Toupet, Loic
, p. 8075 - 8082 (1999)
The total synthesis of L- (or 1S,2R,3S,5S)-bicarbocyclic nucleosides (8- 15) has been accomplished. The key intermediate 3 was synthesized in two steps from the known chiral compound 1 through a stereoselective cyclopropanation under Furukawa conditions and its X-ray structure has been determined. The derivative 4 was utilized to obtain thymine derivative (8). Amino exocyclic pyrimidine (9-12) and purine (13-15) bicarbocyclic L- nucleosides were obtained from the (1S,2R,3S,5S)-2-(3- aminobicyclo[3.1.0]hex-2-yl)ethanol (7).
Bromohydrin reactions of Grieco's bicyclic lactone
Tello-Aburto, Rodolfo,Rios, Maria Yolanda,Swenson, Dale C.,Olivo, Horacio F.
scheme or table, p. 6853 - 6855 (2009/04/07)
The bromohydrin reaction in Grieco's bicyclic lactone 1 was reinvestigated. Two regioisomeric bromohydrins were obtained (2 and 8), and their configurations were unambiguously determined by X-ray diffraction analyses.
Stereoselective synthesis of carbocyclic α-L-homonucleosides
Agrofoglio,Girard,Demaison,Lee,Roingeard,Fridland
, p. 601 - 602 (2007/10/03)
The synthesis of several optically pure carbocyclic α-L-isomeric homonucleosides [3a-e, 6a,b, 7a,b, 10a-d] is reported. The (1R,5S)-2- oxabicyclo[3.3.0]oct-6-en-3-one 1 was used as a chiral starting material.
Synthesis of enantiomerically pure carbocyclic α-L-isomeric homonucleosides
Girard,Demaison,Lee,Agrofoglio
, p. 8745 - 8752 (2007/10/03)
Synthesis of hitherto unknown carbocyclic α-L-isomeric homonucleosides (8a-b, 9a-b) is described. The key intermediate 6 was synthesized from the known compound 1 as a chiral starting material. Construction of the heterocyclic moiety around the amino group of 6 afforded carbocyclic α-L- isomeric 2',3'-dideoxyhomonucleosides 8a-b and their 2',3'-didehydro-2',3'- dideoxy derivatives 9a-b.
A Short and Stereoselective Synthesis of Carbocyclic alpha-L-Dideoxyhomonucleosides
Girard,Lee,Agrofoglio,Fridland
, p. 911 - 913 (2007/10/03)
A stereoselective five-step total synthesis of the hitherto unknown carbocyclic alpha-L-dideoxyhomonucleosides starting from readily available (1R,55)-2-oxabicyclo[3.3.0]oct-6-en-3-one is described.
Novel molecular rearrangements of 4-hydroxy-2-cyclopentenones
novak,Szantay,Meisel,Aszodi,Szabo,fekete
, p. 435 - 450 (2007/10/02)
Novel rearrangements of hydroxycyclopentenone derivatives 1 and 24 to 7,9,11 and 31,33,35 are reported. The stereochemistry of the rearrangement is interpreted as the result of synchronous enolate induced [1.5]-sigmatropic rearrangement and stepwise addition-elimination process. Preparation of the various substrates and structural elucidation of new products are also described.
