π-Facial Selection In Intermolecular Diels-alder Reactions: Total Syntheses of (+)-actinobolin and (+)- 5,6,10-triepi-Actinobolin

Alan P. Kozikowski, Thaddeus R. Nieduzak, Toshiro Konoike, James P. Springer

Research output: Contribution to journalArticlepeer-review

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 languageEnglish (US)
Pages (from-to)5167-5175
Number of pages9
JournalJournal of the American Chemical Society
Volume109
Issue number17
DOIs
StatePublished - Aug 1 1987

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Fingerprint

Dive into the research topics of 'π-Facial Selection In Intermolecular Diels-alder Reactions: Total Syntheses of (+)-actinobolin and (+)- 5,6,10-triepi-Actinobolin'. Together they form a unique fingerprint.

Cite this