After a recent total synthesis had resolved all issues
surrounding
the constitution and stereostructure of prorocentin, it was possible
to devise a new approach aiming at an improved supply of this scarce
marine natural product; this compound is a cometabolite of the prototypical
phosphatase inhibitor okadaic acid but still awaits detailed biological
profiling. The revised entry starts from 2-deoxy-d-glucose;
keys to success were a telescoped hemiacetal reduction/acetal cleavage
and an exquisitely selective gold/Brønsted acid-cocatalyzed spiroacetalization.