Second-Generation Total Synthesis of Prorocentin

Org Lett. 2023 Jul 7;25(26):4903-4907. doi: 10.1021/acs.orglett.3c01720. Epub 2023 Jun 26.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetals / chemistry
  • Enzyme Inhibitors* / chemistry
  • Furans*
  • Okadaic Acid / chemistry
  • Okadaic Acid / pharmacology

Substances

  • prorocentin
  • Okadaic Acid
  • Enzyme Inhibitors
  • Furans
  • Acetals