- Nucleophilic additions to cyclic nitrones en route to iminocyclitols - Total syntheses of DMDP, 6-deoxy-DMDP, DAB-1, CYB-3, nectrisine, and radicamine B
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Highly diastereoselective nucleophilic additions to cyclic nitrones derived from L-malic acid and D-arabinose have been used for the construction of enantiomerically pure polyhydroxylated pyrrolidines. The synthetic strategy adopted was based on an oxidat
- Merino, Pedro,Delso, Ignacio,Tejero, Tomas,Cardona, Francesca,Marradi, Marco,Faggi, Enrico,Parmeggiani, Camilla,Goti, Andrea
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experimental part
p. 2929 - 2947
(2009/04/06)
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- AZA-BENZOFURANYL COMPOUNDS AND METHODS OF USE
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The invention relates to azabenzofuranyl compounds of Formula (I) with anti-cancer and/or anti-inflammatory activity and more specifically to azabenzofuranyl compounds which inhibit MEK kinase activity. The invention provides compositions and methods useful for inhibiting abnormal cell growth or treating a hyperproliferative disorder, or treating an inflammatory disease in a mammal. The invention also relates to methods of using the compounds for in vitro, in situ, and in vivo diagnosis or treatment of mammalian cells, or associated pathological conditions.
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Page/Page column 132
(2008/06/13)
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- GUANIDINO-SUBSTITUTED QUINAZOLINONE COMPOUNDS AS MC4-R AGONISTS
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A variety of small molecule, guanidine-containing molecules capable of acting as MC4-R agonists are provided. The compounds are useful in treating MC4-R mediated diseases when administered to subjects. The compounds have the structure IA, IB, and IC where the values of the variables are defined herein.
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Page/Page column 138-139
(2008/06/13)
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- A new stereospecific synthesis of 1,2,4-Trideoxy-1,4-imino-D-erythro-pentitol
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1,2,4-Trideoxy-1,4-imino-D-erythro-pentitol [(2R,3S)-3-hydroxy-2-hydroxymethylpyrrolidine] (4) was synthesised from 2,5-di-O-tosyl-D-ribono-1,4-lactone in 42 % overall yield. The key steps were deoxygenation at C-2 and a stereospecific inversion of the co
- Malle, Birgitte Molholm,Lundt, Inge,Furneaux, Richard H.
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p. 573 - 583
(2007/10/03)
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- Chromium(II) chloride-mediated coupling reactions of Garner aldehyde with allyl bromides: Facile asymmetric synthesis of (2R,3S)-3-hydroxy-2-hydroxymethylpyrrolidine
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Chromium(II) chloride-mediated coupling reactions of 1,1-dimethylethyl (S)- and (R)-4-formyl-2,2-dimethyloxazolidine-3-carboxylates [(S)- and (R)-Garner aldehydes] (1a,b) with allyl bromides 2a-c proceeded with moderate to good stereoselectivity to give t
- Aoyagi, Yutaka,Inaba, Haruko,Hiraiwa, Yukiko,Kuroda, Asako,Ohta, Akihiro
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p. 3975 - 3978
(2007/10/03)
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- Synthesis of (2R,3S)-3-hydroxy-2-hydroxymethylpyrrolidine from (4S,5S)-3-benzyl-4-formyl-5-vinyl-2-oxazolidinone
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(4S,5S)-3-BenzyI-4-formyl-5-vinyl-2-oxazolidinone (2), readily prepared via the reductive elimination of the mannose-derived iodo phenyl sulfone (6b), is used in the synthesis of the alkaloid (2R,3S)-3-hydroxy-2-hydroxymethylpyrrolidine (1).
- Wee, Andrew G. H.,McLeod, Douglas D.,Rankin, Trent J.
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p. 2263 - 2278
(2007/10/03)
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- A straightforward synthesis of (2S,3R)-3-hydroxyproline and trans-(2R,3S)-2-hydroxymethyl-3-hydroxypyrrolidine
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A stereocontrolled synthesis of (2S,3R)-3-hydroxyproline 1, and trans-(2R,3S)-2-hydroxymethyl-3-hydroxypyrrolidine 2 has been achieved in 21% and 38% yield via the homochiral 4,5-disubstituted oxazolidin-2-one 3. The trans relationship in 2 has been introduced by a modified Mitsunobu reaction.
- Dell'Uomo, Natalina,Di Giovanni, Maria Cristina,Misiti, Domenico,Zappia, Giovanni,Delle Monache, Giuliano
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p. 181 - 188
(2007/10/03)
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- Enantiodivergent synthesis of 2-hydroxymethyl-3-hydroxy-4-nitro-pyrrolidines through tandem Michael-Henry reaction using L-serine as the chiral educt
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By utilizing L-serine, both enantiomers of all trans 2-hydroxymethyl-3-hydroxy-4-nitro-pyrrolidine were efficiently prepared through tandem Michael-Henry methodology. Their stereochemistry has been assigned through conversions of one of them to trans 2-hydroxymethyl-3-hydroxypyrrolidine, a naturally occurring compound recently is isolated from Castanospermum australe.
- Barco, Achille,Benetti, Simonetta,De Risi, Carmela,Pollini, Gian P.,Romagnoli, Romeo,Zanirato, Vinicio
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p. 7599 - 7602
(2007/10/03)
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- Chiral Pool Synthesis of trans-(2S,3S)-3-Hydroxyproline and Castanodiol from S-Pyroglutamic Acid.
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The Pyroglutamic acid derivative 1 was converted through several steps into Castanodiol 9 and 2S,3S-3-Hydroxyproline 11.Key steps of the reaction sequence were the stereoselective epoxidation of 1 to 2 and the regioselective ring opening of 2 to 3.BH3*S(CH3)2 reduction of the amide group of 3 and 4 resulted in a concomitant transformation of the acetal moiety into the N-benzyl protecting group.The air sensitive 5 and 6, were transformed to the stable N-Boc prolinol derivatives 7 and 8.Deprotection of 8 provided 9, while oxidation of 8 gave the protected proline derivative 10.Deprotection of 10 furnished enantiopure 2S,3S-3-Hydroxyproline 11.
- Herdeis, Claus,Hubmann, Hans Peter,Lotter, Hermann
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p. 119 - 128
(2007/10/02)
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- ELECTROPHILIC OLEFIN HETEROCYCLIZATION IN ORGANIC SYNTHESIS. STEREOSELECTIVE INTRAMOLECULAR AMIDOMERCURATION OF γ-HYDROXY-δ,ε-UNSATURATED URETHANES
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Mercuric acetate driven cyclization of γ-hydroxy-δ,ε-unsaturated urethanes 1a,b proceeded regio- and stereoselectively to afford cis-2-acetoxymercurymethyl-3-hydroxypyrrolidines 2a,b, respectively.These were transformed into the key intermediates for seve
- Tkahata, Hiroki,Tajima, Mayumi,Banba, Yasunori,Momose, Takefumi
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p. 2550 - 2552
(2007/10/02)
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- High-Enantioselective Synthesis of Pyrrolidine Derivatives as Chiral Building Blocks
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All four stereoisomers of a pyrrolidine derivative, which is useful as a versatile chiral building block for synthesis of several pyrrolizidine alkaloids, were prepared in high enantioselectivity by utilizing the Sharpless epoxidation of the intermediate
- Hirai, Yoshiro,Chintani, Masaru,Yamazaki, Takao,Momose, Takefumi
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p. 1449 - 1452
(2007/10/02)
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- SYNTHESIS OF (2R,3S)-2-HYDROXYMETHYL-3-HYDROXYPYRROLIDINE AND THE GEISSMAN-WAISS LACTONE FROM (S)-PYROGLUTAMIC ACID
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The synthesis of (2R,3S)- and (2R,3R)-2-hydroxymethyl-3-hydroxypyrrolidine derivatives (5 and 7) and the Geisman-Waiss lactone (12) has been achieved from (S)-pyroglutamic acid.
- Ikota, Nobuo,Hanaki, Akira
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p. 2535 - 2538
(2007/10/02)
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