81052-99-5Relevant articles and documents
Facile access to 4-(1-alkynyl)-2(5H)-furanones by Sonogashira coupling of terminal acetylenes with β-tetronic acid bromide: efficient synthesis of cleviolide
Boukouvalas, John,C?té, Sébastien,Ndzi, Bruno
, p. 105 - 107 (2007)
A mild and convenient synthesis of 4-(1-alkynyl)-2(5H)-furanones has been achieved by Sonogashira or Heck-type alkynylation of β-tetronic acid bromide. As an illustration of this methodology, the natural product cleviolide was prepared in two steps and 78
A concise and efficient novel synthesis of cleviolide
Rossi, Renzo,Bellina, Fabio,Biagetti, Matteo
, p. 3415 - 3420 (1999)
Cleviolide I has been synthesized in 73 % overall yield by a short reaction sequence involving the preparation of 4-methyl-1-trimethylsilylpent- 3-en-1-yne 7 from trimethylsilylethynylzinc chloride 6 and 1-bromo-2- methylpropene 5, the direct conversion of 7 into the corresponding 1- tributylstannyl derivative 8 and the Pd-catalysed reaction of this organotin derivative with 4-bromofuran-2(5H)-one 10.
Vinyl nosylates as partner in copper and silver co-catalyzed Sonogashira cross-coupling reactions
Cheval, Nicolas P.,Hoffmann, Barbara,Dikova, Anna,Sirindil, Fatih,Bertus, Philippe,Blanc, Aurélien,Weibel, Jean-Marc,Pale, Patrick
, p. 7111 - 7119 (2018/11/10)
Vinyl nosylates, readily obtained from β-dicarbonyl derivatives, could be efficiently engaged in Sonogashira cross-coupling reactions, either cocatalyzed by copper or silver salts. The para-nitrobenzenesulfonate (nosylate) group allows this coupling to be performed under very mild conditions (room temperature). These new leaving group and mild conditions could be applied to the synthesis of acetylenic coumarinyl derivatives and to the total synthesis of an acetylenic monoterpene natural product, named cleviolide.
Synthesis of cleviolide and the scobinolides
Hollingworth, Gregory J.,Richecoeur, Alexandre M. E.,Sweeney, Joseph
, p. 2833 - 2836 (2007/10/03)
The palladium-catalysed cross-coupling reaction of 4-tributylstannylfuran-2(5H)-one 3 with 1-iodo-4-methylpent-3-en-1-yne 4a gives the natural product cleviolide; from this substance may be prepared both (Z)- and (E)-isomers of scobinolide.
