38110-76-8Relevant academic research and scientific papers
The Ring Opening of Cyclopentene Oxides by Pyrimidines and Purines as a Pathway to Carbocyclic Nucleoside Analogues
Kapeller,Baumgartner,Marschner,Pucher,Griengl
, p. 953 - 960 (1997)
Various carbocyclic nucleosides with xylo-configuration have been synthesized using ring opening of 5-O-acetyl-1,2-anhydro-3-O-benzylcarba-α-DL-xylo-pentofuranose (6) by thymine, uracil, 4-N-benzoylcytosine, adenine, 6-N-benzoyladenine, and 2-amino-6-chloropurine in alkaline medium. For this purpose, the use of triethylaluminum is introduced into carbanucleoside chemistry. The new method proved to be superior over the application of sodium hydride and potassium or caesium carbonate.
Synthesis of novel, chiral bicyclo[3.1.0]hex-2-ene amino acid derivatives as useful synthons in medicinal chemistry
Stadler, Heinz
, p. 1189 - 1201 (2015/09/28)
A short and concise synthesis of novel, chiral bicyclo[3.1.0]hex-2-ene amino acid derivatives 13 and 14 has been developed. The key step is a stereo- and regioselective allylic amination of exo- and endo-methyl bicyclo[3.1.0]hex-2-ene-6-carboxylates 8 and 9, which were prepared from 7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one (1). These amino acid derivatives are useful building blocks in medicinal chemistry and can be prepared as chiral compounds by using either (+)-1 or (-)-1 as starting material.
Formal synthesis of (±)-mitsugashiwalactone and (±)-isodihydronepetalactone from norborn-5-en-2-one involving shapiro reaction
Chang, Meng-Yang,Chang, Nein-Chen
, p. 41 - 45 (2007/10/03)
A formal synthesis of (±)-mitsugashiwalactone (1) and (±)-isodihydro nepetalactone (2) was accomplished. Baeyer-Villiger lactonization of ketone 9 followed by acidic treatment led to the rearranged lactone 8, which underwent a series of functional group transformations to give cyclopentanone derivatives 19 and 20. Shapiro reaction on 21 and 22 in the presence of excess dry ice gave lactones 5 and 6. Lactones 5 and 6 previously have been converted to mitsugashiwalactone (1) and isodihydronepetalactone (2), respectively.
Allylic Carboxylations and Lactonization Using Benzoquinone and Hydrogen Peroxide or tert-Butyl Hydroperoxide as Oxidants
Akermark, Bjoern,Larsson, E. Magnus,Oslob, Johan D.
, p. 5729 - 5733 (2007/10/02)
Two new systems have been developed for catalytic carboxylation of alkenes.Both use palladium(II) as catalyst and benzoquinone as cocatalyst.In the first hydrogen peroxide was used as oxidant in acetic acid solution.Alkenes such as cyclohexene and 5-decene were converted cleanly to allylic acetates, but with 1-decene mainly the methyl ketone was formed.A diene such as 1,3-cyclohexadiene gave the diacetate while cis-1,2-divinylcyclohexane gave the cyclized monoacetate.In the second system, tert-butyl hydroperoxide was used as oxidant, permitting a wider choice of solvents and nucleophiles.Intramolecular reaction to lactones was possible in addition to allylic addition of acids such as benzoic, pivalic, and (S)-O-acetylmandelic acid.
Efficient Stereocontrolled Total Syntheses of Racemic and Natural Brefeldin-A
Drian, Claude Le,Greene, Andrew E.
, p. 5473 - 5483 (2007/10/02)
Brefeldin-A, an antiobiotic fungal metabolite, has been obtained in both racemic and natural forms through a direct approach that employs norbornenone and 6-heptyn-2-ol as the basic starting materials.
