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.