title: Synthesis of the 2-formylpyrrole spiroketal pollenopyrroside A and structural elucidation of xylapyrroside A, shensongine A and capparisine B.
abstract: A convergent synthesis of the 2-formyl pyrrole spiroketal pollenopyrroside A is reported. The key step involves a Maillard-type condensation of an amine derived from deoxy-d-ribose with a dihydropyranone to furnish the 2-formylpyrrole ring system. Spectroscopic and physical data of 9-epi-pollenopyrroside A are also provided, elucidating the structures of the previously isolated 2-formylpyrrole spiroketals capparisine B, shensongine A and xylapyrroside A.
authors.affiliation: School of Chemical Sciences, University of Auckland, 23 Symonds St, Auckland 1142, New Zealand. m.brimble@auckland.ac.nz.
authors.forename: James M
authors.initials: JM
authors.lastname: Wood
authors.affiliation: School of Chemical Sciences, University of Auckland, 23 Symonds St, Auckland 1142, New Zealand. m.brimble@auckland.ac.nz.
authors.forename: Daniel P
authors.initials: DP
authors.lastname: Furkert
authors.affiliation: School of Chemical Sciences, University of Auckland, 23 Symonds St, Auckland 1142, New Zealand. m.brimble@auckland.ac.nz and Maurice Wilkins Centre for Molecular Biodiscovery, University of Auckland, Private Bag 92019, Auckland 1142, New Zealand.
authors.forename: Margaret A
authors.initials: MA
authors.lastname: Brimble
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D011758:Pyrroles; D013141:Spiro Compounds; C552657:pollenopyrroside A; C000601776:shensongine A