61262-92-8Relevant academic research and scientific papers
Synthesis of four diastereomers of sclerophytin F and structural reassignment of several sclerophytin natural products
Clark, J. Stephen,Delion, La?titia,Farrugia, Louis J.
supporting information, p. 4772 - 4780 (2015/03/18)
Synthesis of the triol that has been proposed to be the marine natural product sclerophytin F has been completed along with the syntheses of three diastereomers. Comparison of the NMR spectroscopic data for all four compounds to the data reported for the natural product reveals that sclerophytin F is not the 3S diastereomer of sclerophytin A as proposed by Friedrich and Paquette. Re-analysis of the NMR spectroscopic data for known sclerophytin natural products and synthetic analogues leads to the conclusion that sclerophytins E and F are the same compound. This finding has allowed structural reassignment of several other cladiellin natural products.
Total synthesis of gonytolides C and G, lachnone C, and formal synthesis of blennolide C and diversonol
Sudhakar, Gangarajula,Bayya, Shruthi,Kadam, Vilas D.,Nanubolu, Jagadeesh Babu
, p. 5601 - 5610 (2014/07/22)
The first stereoselective total synthesis of gonytolide C, which is a monomeric unit of an innate immune promoter gonytolide A, has been accomplished from the aldol reaction between acetophenone derived from orcinol and butyrolactone containing α-keto ester followed by the excellent diastereoselective intramolecular cyclization. The first total synthesis of gonytolide G has been achieved by the oxidation of benzylic methyl in gonytolide C. Additionally, total synthesis of lachnone C and a formal synthesis of blennolide C and diversonol have been achieved by this synthetic method. the Partner Organisations 2014.
SYNTHESIS OF D-AMICETOSE AND L-RHODINOSE FROM L-GLUTAMIC ACID
Berti, Giancarlo,Caroti, Paola,Catelani, Giorgio,Monti, Luigi
, p. 35 - 42 (2007/10/02)
L-Glutamic acid has been converted into a separable mixture of D-amicetono- and L-rhodinono-γ-lactones by a sequence involving transformation into (S)-γ-carboxy-γ-butyrolactone (2), conversion of 2 into the corresponding methyl ketone by the diazoketone route, and selective reduction with zinc borohydride or boranemethyl sulfide.Reduction of the two lactones with di-isobutylaluminium hydride gave the corresponding deoxy sugars.In spite of some improvements in the preparation of 2, the optical yield of this step was only ca. 80percent, but one crystallisation from chloroform raised the optical purity to 96percent.The subsequent steps produced a loss in optical purity of only 4percent.
Regiospecific addition of benzeneselenenyl halide to 1,1-disubstituted olefins
Ho, Pak-Tsun,Kolt, Ralph J.
, p. 663 - 666 (2007/10/02)
The reaction of benzeneselenenyl halide with a variety of 1,1-disubstituted olefins under controlled conditions yields regiospecifically the anti-Markovnikov adducts which have been converted into the synthetically yseful vinyl halides and allyl halides.
