Abstract
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.
Original language | English (US) |
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Pages (from-to) | 5167-5175 |
Number of pages | 9 |
Journal | Journal of the American Chemical Society |
Volume | 109 |
Issue number | 17 |
DOIs | |
State | Published - Aug 1 1987 |
Externally published | Yes |
ASJC Scopus subject areas
- Catalysis
- General Chemistry
- Biochemistry
- Colloid and Surface Chemistry