Total Syntheses of Norrisolide-type Rearranged Spongian Diterpenes Cheloviolene C, Seconorrisolide B, and Seconorrisolide C

The first total syntheses of three unusual norrisolide-type rearranged spongian diterpenes cheloviolene C, seconorrisolide B, and seconorrisolide C have been accomplished via a common intermediate through late stage ring-scissoring. The synthesis features a Wolff ring contraction for the synthesis of the trans-hydrindane system, and a crucial retro Diels-Alder reaction/intramolecular ene cyclization for the rapid stereoselective construction of the furo[2,3-b]furan system, which is commonly seen in rearranged spongian diterpenes.