Total Synthesis of (±)-Streptoglyceride A and of Putative (±)-Streptoglyceride C

The first total synthesis of (±)-Streptoglyceride Aone of the early members of this family to be isolatedhas been accomplished, along with the synthesis of the putative structure of (±)–Streptoglyceride C. The unique tricyclic ring present in these natural products has been constructed by employing a gold-catalyzed tandem diynol cycloisomerization followed by one-pot dihydroxylation/trans-glycosylation. The pendant diene unit was fabricated by Takai olefination and subsequent Stille coupling.