title: Biomimetic synthesis and proposal of relative and absolute stereochemistry of heronapyrrole C.
abstract: The first synthesis of (-)-heronapyrrole C, the enantiomer of a unique farnesylated 2-nitropyrrole natural product is described. With none of the chiral centers of heronapyrrole C originally assigned, we proposed the most likely natural configuration on the basis of a putative biosynthetic pathway. The key step of the synthesis is a biomimetic polyepoxide cyclization cascade to establish the bis-THF moiety. Thus, (-)-heronapyrrole C is synthesized in eight steps from commercially available starting materials.
authors: Fachbereich Chemie, Institut für Organische Chemie, Universität Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany.
authors: Jens
authors: J
authors: Schmidt
authors: Christian B W
authors: CB
authors: Stark
mesh_terms: D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry
chemical_list: C528342:2-nitropyrrole; D011758:Pyrroles; C554880:heronapyrrole C