title: Syntheses of papyracillic acids: application of the tandem chain extension-acylation reaction.
abstract: A synthetic approach to the papyracillic acid family of natural products has been developed. The spiroacetal core is rapidly assembled through an unprecedented zinc carbenoid-mediated tandem chain extension-acylation reaction. Subsequent functional group manipulation provided access to papyracillic acid B and 4-epi-papyracillic acid C. The successful preparation of these molecules resulted in the clarification of structural assignments of members of this family of natural products.
authors.affiliation: Department of Chemistry, University of New Hampshire, Durham, New Hampshire 03824, USA.
authors.forename: Jennifer R
authors.initials: JR
authors.lastname: Mazzone
authors.forename: Charles K
authors.initials: CK
authors.lastname: Zercher
mesh_terms: D000215:Acylation; D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000475:Alkenes; D013141:Spiro Compounds; C547597:papyracillic acid