- New synthesis of important prostanoid intermediate
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New synthesis of intermediates for the preparation of prostaglandin analogs of the E1 series is described. The simple synthesis starts from commercially accessible Corey acetate 1 and makes use of simultaneous protection of the two hydroxy groups in the form of cyclic acetal. No expensive protecting reagents are required and the synthetic sequence leading to the end product is shorter.
- Svoboda, Jiri,Kozmik, Vaclav,Vesely, Ivan,Palecek, Jaroslav
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- New α-methylidenecyclopentenone block from Corey lactone diol
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Methyl (5-methylidene-4-oxocyclopent-2-en-1-yl)acetate was prepared from racemic Corey lactone diol in three steps in 82% overall yield.
- Gimazetdinov, Airat M.,Khalfitdinova, Lena A.,Miftakhov, Mansur S.
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- A NOVEL AND EFFICIENT SYNTHESIS OF 9-(c-4,t-5-BISHYDROXYMETHYLCYCLOPENT-2-EN-r-1-YL)-9H-ADENINE (BCA) HAVING ANTI-HIV ACTIVITY FROM NORBORNADIENE
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9-(c-4, t-5-Bishydroxymethylcyclopent-2-en-r-1-yl)-9H-adenine (BCA: 1), a novel carboxylic nucleoside having significant anti-HIV activity, has been synthesized from norbornadiene.
- Katagiri, Nobuya,Sato, Hiroshi,Arai, Sachie,Toyota, Akemi,Kaneko, Chikara
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p. 1097 - 1100
(2007/10/02)
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- BF3-MEDIATED REACTION OF A SULPHONE WITH ALDEHYDES. A METHOD FOR STEREOSPECIFIC CONSTRUCTION OF PROSTAGLANDIN ω-CHAIN
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A new method for stereospecific construction of the allylic alcohol moiety of prostaglandins, based on application of optically active α-hydroxy aldehydes, is described.In the presence of BF3*Et2O, lithiated sulphones 1 prepared from Corey aldehyde, and carbonyl compounds 2 give the corresponding adducts 3 in moderate to excellent yields, while in the absence of the Lewis acid either no products or only their traces were formed.The addition products 3, in the form of benzoates, mesylates or free alcohols, were subjected to reductive elimination by means of sodium amalgam to give the alkenes 4.Compounds 4d and 4f were transformed into racemic and natural PGF2α, respectively, in line with the known method.
- Achmatowicz, B.,Baranowska, E.,Daniewski, A. R.,Pankowski, J.,Wicha, J.
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p. 4989 - 4998
(2007/10/02)
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