title: Enantioselective synthesis of furo[2,3-b]furans, a spongiane diterpenoid substructure.
abstract: [structure: see text] A short and enantioselective synthesis of cis-fused 5-oxofuro[2,3-b]furans, being found in many spongiane diterpenoid natural products, is reported starting from inexpensive methyl 2-furoate. Moreover, the acid-catalyzed rearrangement of the furo[2,3-b]furan framework A to B is observed for some derivatives, suggesting a simple connection between natural products differing in the absolute configuration of the 3a,6a ring junction.
authors.affiliation: Institut für Organische Chemie der Universität Regensburg, Universitätsstr. 31, D-93053 Regensburg, Germany.
authors.forename: Roland
authors.initials: R
authors.lastname: Weisser
authors.forename: Weimin
authors.initials: W
authors.lastname: Yue
authors.forename: Oliver
authors.initials: O
authors.lastname: Reiser
mesh_terms: D000818:Animals; D002384:Catalysis; D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis*; D005663:Furans / Q000138:chemical synthesis*; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D004224:Diterpenes; D005663:Furans