We have developed an efficient and highly stereocontrolled synthesis of bistramide A, a selective activator of protein kinase C isotype δ. Our synthetic strategy featured a novel bidirectional approach for spiroketal construction based on the ring-opening/cross-metathesis sequence employing a highly strained cyclopropenone acetal. The synthesis afforded the final target with the longest linear sequence of 15 steps and provided unambiguous structural determination of bistramide A, including assignment of the previously unknown C37 stereochemistry.
ASJC Scopus subject areas
- Colloid and Surface Chemistry