Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 32780-06-6, is researched, SMILESS is O=C1O[C@H](CO)CC1, Molecular C5H8O3Journal, Article, Journal of the American Chemical Society called Stereochemical Elucidation of Streptorubin B, Author is Haynes, Stuart W.; Sydor, Paulina K.; Corre, Christophe; Song, Lijiang; Challis, Gregory L., the main research direction is stereochem streptorubin B Streptomyces enantioselective synthesis.Formula: C5H8O3.
Streptorubin B is a structurally remarkable member of the prodiginine group of antibiotics produced by several actinobacteria, including the model organism Streptomyces coelicolor A3. Transannular strain within the pyrrolophane structure of this mol. causes restricted rotation that gives rise to the possibility of (diastereomeric) atropisomers. Neither the relative nor the absolute stereochem. of streptorubin B is known. NOESY NMR experiments were used to define the relative stereochem. of the major atropisomer of streptorubin B·HCl in solution as anti. We exploited this finding together with our knowledge of streptorubin B biosynthesis in S. coelicolor to determine the absolute stereochem. of the anti atropisomer. 2-Undecylpyrrole stereoselectively labeled with deuterium at C-4′ was synthesized and fed to a mutant of S. coelicolor, which was unable to produce streptorubin B because it was blocked in 2-undecylpyrrole biosynthesis, and in which the genes responsible for the last two steps of streptorubin B biosynthesis were overexpressed. 1H and 2H NMR anal. of the stereoselectively deuterium-labeled streptorubin B·HCl produced by this mutasynthesis strategy allowed us to assign the absolute stereochem. of the major (anti) atropisomer as 7’S. HPLC analyses of streptorubin B isolated from S. coelicolor on a homochiral stationary phase and comparisons with streptorubin B derived from an enantioselective synthesis showed that the natural product consists of an approx. 88:7:5 mixture of the (7’S, anti), (7’S, syn), and (7’R, anti) stereoisomers.
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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI