Syntheses of both 5,6,10-friepi-actinobolin and the antibiotic actinobolin are described in which a homochiral diene prepared from L-threonine is employed as a key component in a Diels-Alder reaction with an acetylenic dienophile. While the Diels-Alder reaction of this diene with methyl propiolate furnished the cycloadduct required for the synthesis of (+)-actinobolin as the minor diastereomer, the completion of the synthesis required but seven additional steps. the steric and stercoelectronic features responsible for the π-facial course of this cycloaddition reaction are discussed along with the various steps required to complete the syntheses of the title compounds.
ASJC Scopus subject areas
- Colloid and Surface Chemistry