31753-19-2Relevant articles and documents
Identification of a crucial substructural unit for thromboxane A2 receptor binding
Corey,Su
, p. 2677 - 2680 (1990)
A stereospecific synthesis of the 9α,10α-epoxyprostanoic acid derivative 3, a potent and stable mimic of thromboxane A2, is described.
Chemical transformation of prostaglandin-A2: A novel series of C-10 halogenated, C-12 hydroxylated prostaglandin-A2 analogues
Ratnayake, Anokha S.,Bugni, Tim S.,Veltri, Charles A.,Skalicky, Jack J.,Ireland, Chris M.
, p. 2171 - 2174 (2006)
Synthesis of a novel class of C-10 halogenated and C-12 oxygenated prostaglandin-A2 derivatives (6a-6c) has been accomplished. (15S)-Prostaglandin-A2 (1), from the gorgonian Plexaura homomalla, served as the starting material for the synthesis. The absolute configuration was determined using NMR.
Synthesis of Aromatic Modified Prostaglandins from PGA2
Cai, Zuyun,Nassium, Bahman,Crabbe, Pierre
, p. 1573 - 1578 (2007/10/02)
A general synthetic scheme, starting from PGA2 (obtained from the marine coral Plexaura homomalla), of prostaglandins modified in the upper chain is detailed.Key aldehyde intermediates have been secured from 11-deoxy-PGF2α and PGF2α by an efficient regioselective hydroxylation procedure followed by cleavage of the 5,6-double bond.Witting reaction with these aldehydes provided the novel prostaglandins (5)-(8), belonging to the E and F families, and containing an aromatic ring in the upper chain.
A Triply Convergent Total Synthesis of L-(-)-Prostaglandin E2
Donaldson, R. E.,Saddler, J. C.,Byrn, S.,McKenzie, A. T.,Fuchs, P. L.
, p. 2167 - 2188 (2007/10/02)
This paper details a versatile and efficient total synthesis of l-(-)-PGE2 (3).The key step is a triply convergent conjugate-addition/alkylation reaction involving the 1,4-addition of chiral vinyllithium reagent 7b to chiral vinyl sulfone D-47 to afford sulfone-stabilized anion , which is subsequently alkylated to produce the basic prostaglandin E2 skeleton 70.The synthesis of chiral vinyl sulfone D-47 involves a five step sequence with an enantioconvergent resolution process as one step and produces vinyl sulfone D-47 from readily available sulfide alcohol DL-11 in an overall yield of 36percent.The preparation of D-47 features two steps that utilize stereospecific SN2'reactions.The synthesis of l-(-)-PGE2 (3) involves a seven-step sequence from vinyl sulfone D-47 using mild conditions with an overall yield of 40percent and features an efficient peracetic acid oxidation of secondary amino acid 120 to oximino acid 121, which is, in turn, desulfonylated by 1,4-elimination of phenylsulfinic acid to generate a vinyl nitroso species that undergoes stereospecific 1,4-reduction by sodium borohydride to yield oxime 131.The hydrolysis of oxime 131 to l-(-)-PGE2 (3) using boron trifluoride and paraformaldehyde is the first reported high-yield method (84percent).This gives an overall yield for the synthesis of l-(-)-PGE2 (3) from racemic sulfide alcohol DL-11 of 14.5percent, including the resolution process.
The Total Synthesis of Prostaglandins by the Tropolone Route
Greene, Andrew E.,Teixeira, Marco A.,Barreiro, Eliezer,Cruz, Alicia,Crabbe, Pierre
, p. 2553 - 2564 (2007/10/02)
A general synthesis from α-tropolone methyl ether of natural and modified prostaglandins is detailed.A key intermediate in the synthesis, 7-methoxybicyclohepta-3,6-dien-2-one, has been secured from α-tropolone methyl ether in improved yield and con
8β,12α,15β-PGF2 β Compounds
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, (2008/06/13)
This invention is a group of 8-beta, 12-alpha-PG2 (prostaglandin-type) analogs having variable chain length, or methyl or phenyl substitution in the hydroxy-substituted side-chain, and processes for making them. These compounds are useful for a variety of pharmacological purposes, including anti-ulcer, inhibition of platelet aggregation, increase of nasal patency, and labor inducement at term.
Novel compounds from coral
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, (2008/06/13)
Novel compounds of the formula SPC1 Wherein R1 is hydrogen or methyl, R 2 is hydrogen or acetyl and the diester thereof. The compounds are useful as intermediates for preparing biologically active prostaglandins and they are useful singly as antibacterial agents.