. pi.-Facial selection in intermolecular Diels-Alder reactions: total syntheses of (+)-actinobolin and (+)-5, 6, 10-triepiactinobolin

AP Kozikowski, TR Nieduzak, T Konoike…

文献索引：Kozikowski; Nieduzak; Konoike; Springer Journal of the American Chemical Society, 1987 , vol. 109, # 17 p. 5167 - 5175

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被引用次数: 51

摘要

Abstract: Syntheses of both 5, 6, 10-triepi-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 (+)-actinoblin as the minor diastereomer, the completion of the synthesis ...