21917-20-4Relevant articles and documents
Synthesis of optically pure di- to tetra-substituted cyclopentanes from sugar-derived norbornene derivatives
Horton,Usui
, p. 51 - 59 (1991)
The chiral norbornene derivative 2 obtained from Lewis acid-catalyzed reaction of an L-arabinose-derived dienophile 1 and cyclopentadiene was oxidized with OsO4-NaIO4 to the dialdehyde 3, a tetrasubstituted cyclopentane. Mild treatment of 3 with [Rh(dppp)2]Cl [dppp = Ph2P(CH2)3PPh2] (4) selectively epimerized the aldehyde adjacent to the methoxycarbonyl group to give the epi-aldehyde 8. Under more vigorous conditions, this group was decarbonylated to give the monoaldehyde 11, and more strenuous treatment removed the second aldehyde group to give the didecarbonylated cyclopentane derivative 5. The structure and optical purity of 5 was confirmed by its transformation into (1S,2S)-cyclopentane-1,2-dicarboxylic acid (7). The chiral norbornene derivative 2 obtained from Lewis acid-catalyzed reaction of an L-arabinose-derived dienophile 1 and cyclopentadiene was oxidized with OsO4-NaIO4 to the dialdehyde 3, a tetrasubstituted cyclopentane. Mild treatment of 3 with [Rh(dppp)2]Cl [dppp = Ph2P(CH2)3PPh2] (4) selectively epimerized the aldehyde adjacent to the methoxycarbonyl group to give the epi-aldehyde 8. Under more vigorous conditions, this group was decarbonylated to give the monoaldehyde 11, and more strenuous treatment removed the second aldehyde group to give the didecarbonylated cyclopentane derivative 5. The structure and optical purity of 5 was confirmed by its transformation into (1S,2S)-cyclopentane-1,2-dicarboxylic acid (7).
A cyclopentane conformational restraint for a peptide nucleic acid: Design, asymmetric synthesis, and improved binding affinity to DNA and RNA
Myers, Michael C.,Witschi, Mark A.,Larionova, Nataliya V.,Franck, John M.,Haynes, Russell D.,Hara, Toshiaki,Grajkowski, Andrzej,Appella, Daniel H.
, p. 2695 - 2698 (2007/10/03)
(Matrix presented) A strategy to restrict the highly flexible backbone conformation of a peptide nucleic acid (PNA) by incorporation of a cyclopentane ring is proposed. An asymmetric synthesis of cyclopentane-modified PNA is reported, and its binding prop
Biosynthesis of brefeldin A
Handschin,Sigg,Tamm
, p. 1943 - 1965 (2007/10/05)
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