Organic Letters 2005-11-24

Enantioselective synthesis of furo[2,3-b]furans, a spongiane diterpenoid substructure.

Roland Weisser, Weimin Yue, Oliver Reiser

Index: Org. Lett. 7(24) , 5353-6, (2005)

Full Text: HTML

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.