53138-46-8Relevant academic research and scientific papers
Synthesis of furanone-based natural product analogues with quorum sensing antagonist activity
Hjelmgaard, Thomas,Persson, Tobias,Rasmussen, Thomas B.,Givskov, Michael,Nielsen, John
, p. 3261 - 3271 (2007/10/03)
The synthesis of 5- and 3-(1′-hydroxyalkyl)-substituted 5H-furan-2-ones 4a-d and 8a-d as well as 5-alkylidene-5H-furan-2-ones 5a-d is described. A study of the structure-activity relationship of these furanone-based natural product analogues towards two different quorum sensing systems is reported. Although the synthesized compounds are not as potent quorum sensing inhibitors as some natural counterparts and a synthetic analogue hereof, interesting structure-activity relationships are seen.
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.
Stannylfuranones in synthesis: Highly enantioselective preparation of (+)-hamabiwalactone B
Richecur, Alexandre M.E.,Sweeney
, p. 8901 - 8904 (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 is a Stille coupling of novel stannylfuranone 2 with (E)-iodoalkene 3. The enantiomeric purity of the synthetic natural product was ≥ 99%, as judged by chiral HPLC.
A VERSATILE SYNTHESIS OF 3-SUBSTITUTED 5-ALKYL BUTYROLACTONES VIA DYOTROPIC REARRANGEMENT
Black, T. Howard,Fields, John D.
, p. 125 - 130 (2007/10/02)
Substituted acetic acid dianions are convertable to 3,5-disubstituted butyrolactones, employing a dyotropic rearrangement as the key step.
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.
NEW SYNTHESIS OF Γ-KETO ACIDS FROM NITROOLEFINS AND CARBOXYLIC ACID DIANIONS
Miyashita, Masaaki,Yamaguchi, Ryuji,Yoshikoshi, Akira
, p. 1505 - 1508 (2007/10/02)
As a convenient synthetic method of γ-keto acids, oxoalkylation of carboxylic acids with nitroolefins was examinated.Carboxylic acid dianions reacted with conjugated nitroolefins at low temperature (-100 deg C) and a variety of γ-keto acids were obtained on acidic workup in moderate to good yields.
