- Optimised total syntheses of the F-furan fatty acids F5 and F6 and some deuterated derivatives Dedicated, with the greatest respect, to the memory of Professor Alan R. Katritzky
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Optimised syntheses of F5- and F6-furan fatty acids 2 and 3 are described in full. Key steps include furan formation from a single 3-alkyne-1,2-diol 6 using 5-endo-dig cyclisations triggered by silver(I) nitrate or iodine. Introducti
- Knight, David W.,Smith, Andrew W.T.
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p. 7436 - 7444
(2015/08/24)
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- The preparation of 2,3,5-tri- and 2,3-disubstituted furans by regioselective palladium(0)-catalyzed coupling reactions: Application to the syntheses of rosefuran and the F5 furan fatty acid
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The 5-acceptor-substituted 2,3-dibromofurans 1 and 2 underwent a regioselective Pd0-catalyzed coupling reaction at the C-2 carbon atom. With alkynes the corresponding 2-alkynylfurans 4 and 5 were accessible (49-97% yield) Alkyl-, aryl-, and alk
- Bach, Thorsten,Krüger, Lars
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p. 2045 - 2057
(2007/10/03)
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- Catalytic isomerization of 1-alkynyl-2,3-epoxy alcohols to substituted furans: Succinct routes to furanoid fatty acids and difurylmethanes
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A versatile procedure for the preparation of synthetically valuable 2,5- disubstituted and 2,3,5-trisubstituted furans via mercury(II)-mediated isomerization of 1-alkynyl-2,3-epoxy alcohols is described. Mercury(II)- catalyzed isomerization of alkynyl epoxides 3a-k derived from cyclic α- alkynyl allylic alcohols furnishes 2,3,5-substituted furans bearing an aldehyde or keto group on the C-2 side chain. The reaction is used in a succinct and efficient synthesis of the furanoid fatty acid F5. In contrast, the mercury(II)-catalyzed reaction of a series of alkynyl epoxides 3m-p lacking ring fusion affords difurylmethanes 5, presumably by the dimerization of intermediate 2-(α hydroxyalkyl)furans 4.
- Marson, Charles M.,Harper, Steven
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p. 9223 - 9231
(2007/10/03)
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- Total synthesis of the naturally occurring furanoid fatty acid, F5
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The furanoid fatty acid F5 has been synthesized using a mercury(II) catalyzed isomerization of 2-(1,2-oxiranylcyclododecyl)-3-nonyn-2-ol.
- Marson, Charles M.,Harper, Steven
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p. 333 - 334
(2007/10/03)
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- Sequential Pd(0)-catalyzed reactions for the construction of multiple substituted furans. A short synthesis of the F5 furan fatty acid
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4,5-Dibromofurfural (1) undergoes a regioselective Pd(0)-catalyzed C-C bond forming reaction at its C-5 position to yield corresponding furans 3. The second bromine substituent in C-4 position can be substituted by a methyl group in a subsequent Pd(0)-catalyzed cross coupling reaction. The furan fatty acid 12 and its benzyl ester 13 were prepared in a short synthetic sequence using this method.
- Bach, Thorsten,Krueger, Lars
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p. 1729 - 1732
(2007/10/03)
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