Stereochemical elucidation of streptorubin B

Journal of the American Chemical Society

Volumn 133, Issue 6, 2011, Pages 1793-1798

  Haynes, Stuart W ^a   Sydor, Paulina K ^a   Corre, Christophe ^a   Song, Lijiang ^a   Challis, Gregory L ^a  

^a UNIVERSITY OF WARWICK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ABSOLUTE STEREOCHEMISTRY; ACTINOBACTERIA; ATROPISOMERS; DIASTEREOMERIC; ENANTIOSELECTIVE SYNTHESIS; HOMOCHIRAL; HPLC ANALYSIS; MODEL ORGANISMS; MUTASYNTHESIS; NATURAL PRODUCTS; NMR ANALYSIS; RESTRICTED ROTATIONS; S. COELICOLOR; STATIONARY PHASE; STREPTOMYCES COELICOLOR A3(2);

BIOCHEMISTRY; BIOSYNTHESIS; DEUTERIUM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

STEREOCHEMISTRY;

DEUTERIUM; HYDROCHLORIC ACID; POLYPEPTIDE ANTIBIOTIC AGENT; PYRROLE DERIVATIVE; STREPTORUBIN B; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL GENE; BIOSYNTHESIS; CHIRALITY; CONTROLLED STUDY; DEUTERON NUCLEAR MAGNETIC RESONANCE; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; GENE OVEREXPRESSION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STEREOISOMERISM; STREPTOMYCES COELICOLOR;

ANTI-BACTERIAL AGENTS; DEUTERIUM; MAGNETIC RESONANCE SPECTROSCOPY; PRODIGIOSIN; PROTONS; SOLUTIONS; STEREOISOMERISM; STREPTOMYCES COELICOLOR;

EID: 79951534830     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja109164t     Document Type: Article

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32. (7′ R, syn)-streptorubin B (retention time ? 10 minutes) could be detected in the samples of synthetic (7′ RS) and (7′ R)-streptorubin B (see the Supporting Information). It was not detectable in the sample of streptorubin B isolated from S. coelicolor because it constitutes only ∼0.5% of the mixture [the anti/syn ratio is ∼88:7 and only ∼5% of (7′ R, anti)-streptorubin B is present in the natural product].
33. 4 would also reduce the ester in 13 to the corresponding alkoxide, which would be expected to displace iodide in an intramolecular reaction to form the corresponding tetrahydrofuran. Thus, a different synthetic approach for the stereospecific deuterium-labeling of 2-undecylpyrrole at C-4′ would be required.