320742-72-1Relevant academic research and scientific papers
Unexpected stereochemical tolerance for the biological activity of tyroscherin
Tae, Hyun Seop,Hines, John,Schneekloth, Ashley R.,Crews, Craig M.
, p. 1708 - 1713 (2011/04/22)
Here we describe the concise syntheses of the 15 diastereomers and key analogs of the natural product tyroscherin. While systematic analysis of the analogs clearly demonstrated that the hydrocarbon tail is important for biological activity, structure-activity relationship studies of the complete tyroscherin diastereoarray revealed a surprisingly expansive stereochemical tolerance for the cytotoxic activity. Our results represent a departure from the tenet that biological activity is constrained to a narrow pharmacophore, and highlight the recently emerging appreciation for stereochemical flexibility in defining the essential structural elements of biologically active small molecules.
An expeditious total synthesis of kalkitoxins: Determination of the absolute stereostructure of natural kalkitoxin
Yokokawa, Fumiaki,Asano, Toshinobu,Okino, Tatsufumi,Gerwick, William H.,Shioiri, Takayuki
, p. 6859 - 6880 (2007/10/03)
Kalkitoxin, a potent neurotoxin isolated from the marine cyanobacteria Lyngbya majuscula, and its congeners (1-7) were efficiently synthesized utilizing Hruby's diastereoselective 1,4-addition and the Wipf's oxazoline-thiazoline conversion as key steps. T
A Novel Approach toward the Synthesis of Kendomycin: Selective Synthesis of a C-Aryl Glycoside as a Single Atropisomer
Pichlmair, Stefan,Marques, Maria M. B.,Green, Martin P.,Martin, Harry J.,Mulzer, Johann
, p. 4657 - 4659 (2007/10/03)
(Matrix presented) A convergent and concise route to an advanced precursor 2b of kendomycin (1) has been developed by applying a SN1 ring cyclization as a key step. The resulting C-aryl glycoside was initially isolated as a rotameric mixture, b
