title: Total synthesis of heronapyrrole C.
abstract: A flexible total synthesis of the 2-nitropyrrole-derived marine natural product, (+)-heronapyrrole C, is reported. The approach is based on regioselective access to key building blocks containing the rare 4-substituted 2-nitropyrrole motif. Sharpless asymmetric epoxidation and dihydroxylation and a Shi epoxidation were used to introduce the five stereogenic centers of the bis-THF-diol side chain. The N-benzoyloxymethyl (Boz) protecting group was crucial for functionalization of the 2-nitropyrrole moiety and enabling final deprotection under mild conditions.
authors.affiliation: School of Chemical Sciences, The University of Auckland , 23 Symonds St., Auckland 1000, New Zealand.
authors.forename: Xiao-Bo
authors.initials: XB
authors.lastname: Ding
authors.forename: Daniel P
authors.initials: DP
authors.lastname: Furkert
authors.forename: Robert J
authors.initials: RJ
authors.lastname: Capon
authors.forename: Margaret A
authors.initials: MA
authors.lastname: Brimble
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry
chemical_list: C528342:2-nitropyrrole; D001688:Biological Products; D011758:Pyrroles; C554880:heronapyrrole C