- Facile synthesis of 6a-carbaprostaglandin I2
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The optically active 6a-carbaprostaglandin I2 (2), a stable mimic of natural prostacyclin (1), was synthesized from the lactone 4 or the hydroxy acid 5, which were general synthetic intermediates for natural prostaglandins.
- Konishi, Yoshitaka,Kawamura, Masanori,Iguchi, Yoichi,Arai, Yoshinobu,Hayashi, Masaki
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p. 4391 - 4399
(2015/01/08)
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- Cross metathesis as a general strategy for the synthesis of prostacyclin and prostaglandin analogues
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A cross metathesis (CM) approach has been successfully applied to introduce fully functionalized ω-side chain appendages of various prostacyclin and prostaglandin analogues, resulting in high (E)-selectivities for the C13-C14 double bond and leading to the total syntheses of isocarbacyclin, 15R-TIC, carbacyclin, and PGF2α, and the formal syntheses of 15-deoxy-TIC and PGJ2.
- Sheddan, Neil A.,Mulzer, Johann
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p. 3101 - 3104
(2007/10/03)
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- PROSTANOIDS. LII. (+/-)-7,7-DICHLORO-4β-TRIMETHYLSILYLBICYCLOHEPT-3-EN-6-ONE IN THE SYNTHESIS OF PROSTANOIDS. RACEMIC CARBACYCLIN
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The products from the Prins reaction of formaldehyde and (+/-)-7,7-dichloro-4β-trimethylsilylbicyclohept-3-en-6-one were isolated and characterized.The optimum conditions were found for the production of the isomeric 2β-acetoxy-6,6(7,7)-dichlorobicyclohept-3-en-7(6)-ones and 2β-acetoxymethyl-3α-acetoxy-6,6(7,7)-dichlorobicyclohept-3-en-7(6)-ones and also (1R,2S,5R,6S,10R)-3,3-dichloro-4-oxo-10-hydroxy(acetoxy)-8-oxatricyclo2,5>undecanes, suitable for the subsequent synthesis of modified prostanoids.An effective scheme for the synthesis of (+/-)-carbacyclin was worked out on the basis of the monoacetates of a series of bicycloheptenones through the corresponding 2β-acetoxymethyl-3α-acetoxybicyclooctan-7-ones.
- Tolstikov, G. A.,Akhmetvaleev, R. R.,Zhurba, V. M.,Vasil'eva, M. S.,Miftakhov, M. S.
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p. 543 - 552
(2007/10/02)
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- A NEW SYNTHESIS OF (+)-6a-CARBAPROSTAGLANDIN I2 EMPLOYING YEAST REDUCTION OF A β-KETO ESTER DERIVED FROM cis-BICYCLOOCTANE-3,7-DIONE AS THE KEY-STEP
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(+)-6a-carbaprostaglandin I2 (carbacyclin), a stable mimic of prostaglandin I2 (prostacyclin), was synthesized by utilizing the kinetic resolution of (+/-)-2-ethoxycarbonyl-7,7-ethylenedioxybicyclooctan-3-one in the course of its yeast reduction as
- Mori, Kenji,Tsuji, Masahiro
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p. 435 - 444
(2007/10/02)
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- SYNTHESIS OF CARBACYCLIN USING RHODIUM(I) COMPLEX
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The key intermediate (11) for the synthesis of carbacyclin (1) was synthesized by the application of a new method for stereoselective five-membered ring formation using Wilkinson complex. KEYWORDS --- carbacyclin; Wilkinson complex; cyclization; five-memb
- Ueno, Kohshi,Suemune, Hiroshi,Sakai, Kiyoshi
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p. 3768 - 3769
(2007/10/02)
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- Synthesis of Stable Prostacyclin Analogues from 2,3-Disubstituted Bicycloheptan-6-ones
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A short synthesis of 9-deoxy-6-9α-methanoepoxy-Δ5-prostaglandin F1 (14) from bicycloheptan-6-one (3) is described.The ketone (3) can be converted by known methods into the vinyl ether (8).In the presence of mercury(II) acetate at 100 deg C, the 5-hydroxyalk-1-enyl methyl ether (8) undergoes a novel intramolecular vinyl transetherification reaction to give the Δ2-dihydropyran (9).Hydroboration-oxidation of the dihydropyran (9) furnished selectively the tetrahydropyran-3-ol (10).Subsequent elaboration via oxidation, Wittig olefination, and deprotection afforded 9-deoxy-6,9α-methanoepoxy-Δ5-prostaglandin F1 (14).The protected bicycloheptan-6-one (16) underwent a ring expansion with diazomethane, producing a 1:1 mixture of the two homologated ketones (17) and (18).Wittig olefination and deprotection of these ketones provided 15-epi-9-deoxy-6,9α-methano-Δ5-prostaglandin F1 (19) and its structural isomer (20).The two bicycloheptan-6-ones (3) and (4) also led directly to a series of 9-deoxy-6,9α-cycloprostaglandins F1 via Wittig reactions.
- Newton, Roger F.,Wadsworth, Alan H.
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p. 822 - 830
(2007/10/02)
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- Facile synthesis of 6a-carbaprostaglandin I2
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The optically active 6a-carbaprostaglandin I2 (2), a stable mimic of natural prostacyclin (1), was synthesized from the lactone 4 or the hydroxy acid 5, which were general synthetic intermediates for natural prostaglandins.
- Konishi, Yoshitaka,Kawamura, Masanori,Iguchi, Yoichi,Arai, Yoshinobu,Hayashi, Masaki
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p. 4391 - 4399
(2014/12/10)
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