Structure and Total Synthesis of Sporol and Neosporol

Abstract

The complete details of the synthesis of sporol (1) and its formerly assigned structure, neosporol (2), are provided. A highly stereoselective Claisen rearrangement sets the C5–C6 stereochemistry of the trichothecene skeleton. Subsequent functional group manipulation and ring closures led to the pentacyclic structures. The 1H NMR studies that led to the structure reassignment are also discussed. © 1993, American Chemical Society. All rights reserved.