53138-50-4Relevant academic research and scientific papers
Preparation of (+)-Hamabiwalactone B via Stille coupling of an enantiomerically pure stannylfuranone
Richec?ur, Alexandre M. E.,Sweeney
, p. 389 - 395 (2007/10/03)
An unambiguous and highly enantioselective total synthesis of the naturally occurring 2(5H)-furanone Hamabiwalactone B has been achieved. The key step was a palladium-catalysed cross coupling ('Stille' coupling) of the previously unreported stannylfuranone 2 with (E)-iodoalkene 3. The enantiomeric purity of the synthetic natural product was ≥99%, as judged by chiral HPLC. (C) 2000 Elsevier Science Ltd.
Michael Reaction of Conjugated Nitro Olefins with Carboxylic Acid Dianions and with Ester Enolates: New Synthesis of γ-Keto Acids and γ-Keto Esters
Miyashita, Masaaki,Yamaguchi, Ryuji,Yoshikoshi, Akira
, p. 2857 - 2863 (2007/10/02)
Base-sensitive conjugated nitro olefins 2 reacted with lithium dianions of carboxylic acids 3 or with lithium enolates of esters 4 at a low temperature of ca. -100 deg C, and subsequent treatment of the Michael adducts with aqueous acid yielded γ-keto acids 5 or esters 5' in a one-pot operation, respectively.Results of both the reactions have been compared.Some applications of the resulting γ-keto esters in organic synthesis have also been demonstrated in lactone synthesis and cyclenone annulation.
