- Synthesis of tritium-labelled isocarbacyclin derivatives, radiolabelled prostaglandin I1 analogs(1)
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Three tritiated isocarbacyclin [9 (O) -metano-Δ6(9α) - prostaglandin I1] derivatives, [11-3H]-isocarbacyclin methyl ester (7a), [11-3H] - (17S)-17-methyl-20-homoisocarbacyclin (9), and its methyl ester (8a) were synthesized. Tritium was introduced to the 11-position via [3H]-sodium tetrahydroborate reduction of 11-dehydro-isocarbacyclin intermediates 10 and 11.
- Sugiura, Satoshi,Kurozumi, Seizi,Ikegami, Shiro
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p. 128 - 138
(2007/10/03)
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- Short synthesis of isocarbacyclin by regioselective SN2′ alkylation of bicyclic allylic esters with zinc-copper reagents
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Isocarbacyclin [(+)-9(0)-methano-Δ6(9α)-prostaglandin I1] (2) was synthesized from bicyclic synthons such as 2-phosphorylated, 2-(thio)phosphorylated, 2-tosylated, 2-methoxycarbonylated, and 2-chloro-3-methylenebicyclo[3.3,0]octanes via highly regioselective SN2′ alkylation with zinc-copper reagents 9 in excellent yields.
- Tanaka, Toshio,Bannai, Kiyoshi,Hazato, Atsuo,Koga, Masahiro,Kurozumi, Seizi,Kato, Yoshinori
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p. 1861 - 1876
(2007/10/02)
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- Isocarbacyclin derivatives and process for production thereof
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An isocarbacyclin derivative represented by the general formula STR1 wherein R1 represents a linear, branched or cyclic alkyl, alkenyl or alkynyl group having 5 to 10 carbon atoms, and R2 and R3 represent a hydrogen atom or a protective group for the hydroxyl group; and a process for production thereof.
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- Novel isocarbacyclins and processes for production thereof
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A novel isocarbacyclin which is a compound represented by the following formula STR1 wherein R1 represents a hydrogen atom, or a C1 -C4 alkyl or alkenyl group; R2 and R3 are identical or different and each represents a hydrogen atom, a tri(C1 -C7)hydrocarbon-silyl group or a group forming an acetal linkage together with the oxygen atom of the hydroxyl group; R4 represents a hydrogen atom, a methyl group or a vinyl group; R5 represents an unsubstituted linear or branched C3 -C8 alkyl group which may be interrupted by an oxygen atom, a substituted linear or branched C1 -C5 group in which the substituent is a C1 -C6 alkoxy group or a phenyl, phenoxy or C3 -C10 cycloalkyl group which may be substituted further, a phenyl group which may be substituted, a phenoxy group which may be substituted, or a C3 -C10 cycloalkyl group which may be substituted; n is 0 or 1; and Ar represents a substituted or unsubstituted phenyl group, its enantiomorph, or a mixture both in an arbitrary ratio.
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- PRACTICAL SYNTHESIS OF (+)-9(O)-METHANO-Δ6(9α)-PGI1. THE HIGHLY POTENT CARBON ANALOG OF PROSTACYCLIN
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A practical synthesis of (+)-9(O)-methano-Δ6(9α)-PGI1, potentially a useful therapeutic agent, has been accomplished by utilizing the intramolecular aldol condensation as key step followed by the Wittig reaction and the regioselective hydrogenation.
- Sodeoka, Mikiko,Shibasaki, Masakatsu
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p. 579 - 582
(2007/10/02)
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- AN IMPROVED ROUTE TO (+)-9(O)-METHANO-Δ6(9Α)-PROSTAGLANDIN-I1 (ISOCARBACYCLIN)
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An improved synthesis of the title compound and a synthesis of its derivatives are described, in which the regiospecific transformation of the diene into diol was effectiely achived by using thexylborane.
- Torisawa, Yasuhiro,Okabe, Hiromitsu,Shibasaki, Masakatsu,Ikegami, Shiro
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p. 1069 - 1072
(2007/10/02)
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- THE INTRAMOLECULAR THERMAL ENE REACTION ROUTE TO (+)-9(O)-METHANO-Δ6(9α)-PGI1
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(+)-9(O)-Methano-Δ6(9α)-PGI1, a more potent carbon analog than carbacyclin, has been synthesized from the Corey lactone by utilizing the intramolecular thermal ene reaction as a key step.
- Ogawa, Yuji,Shibasaki, Masakatsu
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p. 1067 - 1070
(2007/10/02)
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- Synthesis of 9(0)-methano-Δ6(9α)-PGI1: The highly potent carbon analog of prostacyclin
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A new prostacyclin analog, 9(o)-methano-Δ6(9α)-PGI1, was synthesized by utilizing intramolecular pinacolic coupling reaction as the key step and was shown to be more potent than carbacyclin in inhibition of platelet aggregation.
- Shibasaki,Torisawa,Ikegami
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p. 3493 - 3496
(2007/10/02)
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- REGIOCONTROLLED CONVERSION OF α,α-UNSATURATED KETONES TO OLEFINS VIA ALLYLSILANES: SYNTHESIS OF dl-9(O)-METHANO-Δ6(9α)-PGI1
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A synthesis of dl-9(O)-methano-Δ6(9α)-PGI1 (1), a more potent prostacyclin analog than carbacyclin, has been accomplished utilizing regiocontrolled transformation of the enone to the olefin via the allylsilane as a key step.
- Shibasaki, Masakatsu,Fukasawa, Hidemi,Ikegami, Shiro
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p. 3497 - 3500
(2007/10/02)
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