Enantioselective synthesis of furo[2,3-b]furans, a spongiane diterpenoid substructure.
[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.
Weisser
Roland
R
Institut für Organische Chemie der Universität Regensburg, Universitätsstr. 31, D-93053 Regensburg, Germany.
Yue
Weimin
W
Reiser
Oliver
O
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
D004224:Diterpenes; D005663:Furans