172995-43-6Relevant articles and documents
Synthesis and biological properties of tensyuic acids B, C, and E, and investigation of the optical purity of natural tensyuic acid B
Matsumaru, Takanori,Sunazuka, Toshiaki,Hirose, Tomoyasu,Ishiyama, Aki,Namatame, Miyuki,Fukuda, Takashi,Tomoda, Hiroshi,Otoguro, Kazuhiko,Omura, Satoshi
, p. 7369 - 7377 (2008/12/20)
The first, concise total synthesis of (±)-tensyuic acids B, C, and E, using chemoselective formal SN2′ type Grignard reactions and selective esterification, is described. In addition, the optical purity of natural (±)-tensyuic acid B was determined using Chirabite-AR. Synthetic tensyuic acids, together with their intermediate compounds, were found to possess useful bioactive properties, with some of them showing potent activity against Trypanosoma brucei brucei strain GUTat 3.1.
Total synthesis of cytotoxic sponge alkaloids hachijodines F and G
Goundry, William R.F.,Lee, Victor,Baldwin, Jack E.
, p. 2745 - 2747 (2007/10/03)
The total synthesis of two cytotoxic sponge alkaloids hachijodines F (1) and G (2) via a common intermediate 3 is described.
Structure determination of an endogenous sleep-inducing lipid, cis-9-octadecenamide (oleamide): A synthetic approach to the chemical analysis of trace quantities of a natural product
Cravatt, Benjamin F.,Lerner, Richard A.,Boger, Dale L.
, p. 580 - 590 (2007/10/03)
The pursuit of endogenous sleep-inducing substances has been the focus of an extensive, complicated body of research. Several compounds, including Δ-sleep-inducing peptide and prostaglandin D2, have been suggested to play a role in sleep induction, and yet, the molecular mechanisms of this physiological process remain largely unknown. In recent efforts, the cerebrospinal fluid of sleep-deprived cats was analyzed in search of compounds that accumulated during sleep deprivation. An agent with the chemical formula C18H35NO was found to cycle with sleep-wake patterns, increasing in concentration with sleep deprivation and decreasing in amount upon recovery sleep. Since the material was generated in minute quantities and only under the special conditions of sleep deprivation, efforts to isolate sufficient material for adequate characterization, structure identification, and subsequent detailed evaluation of its properties proved unrealistic. With the trace amounts of the impure endogenous compound available, extensive MS studies on the agent were completed, revealing key structural features of the molecule including two degrees of unsaturation, a long alkyl chain, and a nitrogen substituent capable of fragmenting as ammonia. Additionally, HPLC traces suggested a weak UV absorbance for the unknown material. With this data in hand and encouraged by the relatively small size of the molecule, MW = 281, a synthetic approach toward the structural identification of the natural compound was initiated. Herein, we report the full details of the synthesis and comparative characterization of candidate structures for this endogenous agent that led to the unambiguous structural correlation with synthetic cis-9-octadecenamide.
