- Sarkomycin a methyl esters and functionalized cyclopentane blocks for brefeldin a
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Sarkomycin A methyl esters and functionalized cyclopentane blocks for brefeldin A were synthesized starting from diastereoisomeric (1R,2S)-and (1S,2R)-2-hydroxymethyl-N-[(1R)-1-phenylethyl]cyclopent-3-ene-1-carboxamides. Pleiades Publishing, Ltd., 2012.
- Gimazetdinov,Ishmurzina,Miftakhov
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experimental part
p. 8 - 17
(2012/05/20)
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- Synthesis of enantiomeric cyclosarcomycins
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Based on chiral cyclopentene blocks 2 and 3, enantiomeric cyclosarcomycins 4 and 5 were obtained and characterised.
- Gimazetdinov, Airat M.,Gimazetdinova, Tat'yana V.,Miftakhov, Mansur S.
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experimental part
p. 15 - 16
(2010/04/23)
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- An integrated chemoenzymatic synthesis of enantiopure (-)-(1R,5S)-cyclosarkomycin: A sarkomycin precursor
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A five-step chemoenzymatic synthesis of (-)-(1R,5S)-cyclosarkomycin 2 has been achieved starting from commercial racemic bicycloheptenone 3. The strategy developed involved - as key steps - an enantioselective microbiologically catalyzed Baeyer-Villiger oxidation followed by a chemical regioselective epoxide ring opening.
- Andrau, Laura,Lebreton, Jacques,Viazzo, Pascale,Alphand, Veronique,Furstoss, Roland
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p. 825 - 826
(2007/10/03)
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- Diastereoselective iodocarbocyclization reaction of 2- or 3-oxy-4-pentenylmalonate derivatives
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1,2- Or 1,3-asymmetric induction in the iodocarbocyclization reaction of 4-pentenylmalonate derivatives having a stereogenic center at an allylic or a homoallylic position has been investigated. The iodocarbocyclization reactions of 3-oxy-4-pentenylmalonate derivatives proceeded with high cis-selectivity through stereoelectronic control of the oxygenated substituent at an allylic position. In the reaction of (S)-2-siloxy-4-pentenylmalonate, an excellent diastereoselectivity was achieved through the utilization of double stereodifferentiation with a chiral titanium catalyst. Furthermore, as an application of the present reaction, the asymmetric syntheses of cyclosarkomycin and a synthetic intermediate of brefeldin A from optically pure 2- and 3-oxy-4-pentenylmalonate derivatives are also described.
- Inoue, Tadashi,Kitagawa, Osamu,Oda, Yoko,Taguchi, Takeo
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p. 8256 - 8263
(2007/10/03)
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- DIASTEREOSELECTIVE IODOCARBOCYCLIZATION OF 4-PENTENYLMALONATE DERIVATIVES: APPLICATION TO CYCLOSARKOMYCIN SYNTHESIS
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The iodocarbocyclization of 4-pentenylmalonate 1 having a substituent at the 2 or 3 position effectively proceeded by treating 1 with I2 and Ti(OtBu)4 in the presence of CuO.Stereoelectronic effect of the substituent at allylic position on diastereoselect
- Kitagawa, Osamu,Inoue, Tadashi,Taguchi, Takeo
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p. 1059 - 1062
(2007/10/02)
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- A NEW APPROACH TO CYCLOPENTANE ANNULATED COMPOUNDS VIA 1-(CYCLOPENT-1-ENYLCARBONYL)VINYLPHOSPHONATES, AND SYNTHESIS AND SYNTHETIC APPLICATION OF α-DIETHOXYPHOSPHORYL-Δα,β-BUTENOLIDES
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Fused ring systems, containing two or three five-membered rings, were constructed by utilizing 1-(cyclopent-1-enylcarbonyl)vinylphosphonates which function as versatile annulating agents.Facile synthesis of α,β-carbocyclic fused γ-lactones was provided by
- Minami, Toru,Nakayama, Minoru,Fujimoto, Kouichi,Matsuo, Shingo
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p. 135 - 138
(2007/10/02)
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- ASYMMETRIC DIELS-ALDER REACTIONS: EPC-SYNTHESIS OF A STABLE SARKOMYCIN PRECURSOR (CYCLOSARKOMYCIN)
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The first synthesis of enantiomerically pure cyclosarkomycin, a stable, crystaline precursor of the antitumor agent sarkomycin is reported.Key steps are an asymmetric Diels-Alder reaction of the (E)-3-bromoacrylate of (R)-pantolactone and introduction of oxygen funtionality via elimination/β-addition.The synthesis of cyclosarkomycin was accomplished in 9 steps in 17 percent overall yield.
- Linz, Guenter,Weetman, John,Hady, A. F. Abdel,Helmchen, Guenter
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p. 5599 - 5602
(2007/10/02)
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- Trapping of Cyclopentadienone as a 4? Component in Diels-Alder Reactions with Ethyl Acrylate: a Simple Synthesis of (+/-)-Sarkomycin
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The ability of cyclopentadienone to act as the diene counterpart in Diels-Alder reactions was demonstrated through the isolation of the cycloadduct with ethyl acrylate, which was utilized as the starting point for an expeditious synthesis of (+/-)-sarkomycin.
- Baraldi, Pier Giovanni,Barco, Achille,Benetti, Simonetta,Pollini, Gian Piero,Polo, Eleonora,Simoni, Daniele
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p. 1049 - 1050
(2007/10/02)
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- A DIRECT ORGANOCOBALT MEDIATED SYNTHESIS OF SUBSTITUTED 3-OXABICYCLOOCT-7-EN-ONES
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Substituted 3-oxabicyclooct-7-en-6-ones may be synthesised directly by reaction of alkyne hexacarbonyldicobalt complexes with 2,5-dihydrofurans; this strategy is illustrated by very brief total syntheses of cyclomethylenomycin A (2) and cyclosarkomycin (4).
- Billington, David C.
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p. 2905 - 2908
(2007/10/02)
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- Regiospecific Synthesis of Sarkomycin and Some Analogues
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The first regiospecific total synthesis of the anticancer compound sarkomycin (1) is described.The starting material is 2-(carbomethoxycyclopent-2-enone (4), a useful precursor for cyclopentanoid natural products.The cyano derivative 5, the amide derivative 6, and the keto lactone 9 were also synthetized.The latter may be considered as a "cyclized" form of sarkomycin and was shown to open slowly to the natural product upon treament with dilute acid.
- Marx, John N.,Minaskanian, Gevork
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p. 3306 - 3310
(2007/10/02)
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