4157-02-2Relevant articles and documents
Catalytic asymmetric desymmetrization of cyclic meso-1,3- and 1,4-diols by a phosphinite derivative of quinidine
Mizuta, Shinya,Tsuzuki, Takeo,Fujimoto, Tetsuya,Yamamoto, Iwao
, p. 3633 - 3635 (2005)
(Chemical Equation Presented) Asymmetric monobenzoylation reactions of cyclic meso-1,3- and 1,4-diols were catalyzed by a phosphinite derivative of quinidine to afford the corresponding monobenzoylated diol with good yield and enantioselectivity.
ACYLATION ENANTIOSELECTIVE D'UN DIOL MESO: LE CIS-CYCLOPENTENE-2 DIOL-1,4
Duhamel, Lucette,Herman, Thierry
, p. 3099 - 3102 (1985)
Optically active monobenzoate of cis-2-cyclopenten-1,4-diol is obtained by enantioselective acylation of the meso diol by benzoylchloride in the presence of tertiary chiral amines.
Synthesis and binding properties of cyclopentane analogues of myo-inositol 1,4,5-tris(phosphate)
Moris, Marc-Antoine,Caron, Annabelle Z.,Guillemette, Gaetan,Schlewer, Gilbert
, p. 3995 - 4001 (2007/10/03)
Cyclopentanic analogues of myo-inositol 1,4,5-tris(phosphate) were synthesised starting from cyclopentadiene. The affinities of the trisphosphorylated derivatives for the Ins(1,4,5)P3 receptors were equipotent to that of compound 4, showing that the relative orientation of the functional groups, particularly of the hydroxyl, is not of prime importance in this series. The 31P NMR titration curves show that the tris(phosphate) 5 behaves as the superimposition of an independent phosphate and a vicinal bis(phosphate).
Catalytic asymmetrization of cis-2-cyclopentene-1,4-diol. Highly efficient and practical synthesis of (R)-4-benzoyloxy-2-cyclopenten-1-one
Oriyama, Takeshi,Hosoya, Takeshi,Sano, Tomohumi
, p. 1065 - 1069 (2007/10/03)
Highly efficient, direct, and practical synthesis of (R)-4-benzoyloxy-2- cyclopenten-1-one, a chiral building block for various prostaglandins, with excellent ee was performed by the catalytic asymmetric acylation of cis-2- cyclopentene-1,4-diol, followed by oxidation with PDC.
A PALLADIUM-CATALYZED ROUTE TO MONO- AND DIPROTECTED CIS-2-CYCLOPENTENE-1,4-DIOLS
Deardorff, Donald R.,Myles, David C.,MacFerrin, Kurtis D.
, p. 5615 - 5618 (2007/10/02)
The ?-allylpalladium complex arising from cyclopentadiene monoepoxide has been shown to react with carboxylic acids and derivatives both as a nucleophile and an electrophile.This reaction represents an attractive synthetic route to protected versions of cis-2-cyclopentene-1,4-diol.
STEREOCHEMICAL STUDIES - LVII. SYNTHESIS OF OPTICALLY ACTIVE COMPOUNDS BY THE NOVEL USE OF MESO-COMPOUNDS -1. EFFICIENT SYNTHESIS OF TWO STRUCTURAL TYPES OF OPTICALLY PURE PROSTAGLANDIN INTERMEDIATES.
Nara, M,Terashima, S.,Yamada, S.
, p. 3161 - 3170 (2007/10/02)
With an aim to overcome several inefficient aspects of ordinary methods of preparing optically active compounds, we have developed a new method which recommends utilization of symmetrically functionalized meso-compounds in place of racemic compounds.As shown in Scheme 1, when the meso-compound (I) is monofunctionalized by an optically active functional group (A) and each of the formed diastereomers (II and III) is subjected to further chemical elaborations including protective group transposition, it is theoretically possible to convert the total amount of the starting material (I) into the requisite optically pure product (VI or VII) by selecting synthetic schemes.By employing this novel concept, two structural types of the prostaglandin intermediates ((-)- and (+)-2a,b) have been prepared from the meso-diols (1a,b) by way of the two diastereomeric monoesters (13a,b and 14a,b) which are produced by the reactions 1a,b with N-mesyl- and N-phthaloyl-(S)-phenylalanyl chloride (3a,b).
