Further studies of the Daphniphyllum alkaloid polycyclization cascade |
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Authors: | Wallace G A Heathcock C H |
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Institution: | Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley, California 94720, USA. |
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Abstract: | The scope of the 2-azadiene intramolecular Diels-Alder cyclization, previously employed for synthesis of the Daphniphyllum alkaloids, has been further investigated. Through a series of 1,5-diol cyclization precursors the substitution pattern of both the dienophile and the 2-azadiene were examined. From these studies it was shown that the cascade reaction is tolerant toward a variety of alkyl-substituted dienophiles. However, it was also demonstrated that this reaction is very sensitive to the substitution pattern of the 2-azadiene. Alterations made to the structure of the 2-azadiene cause either competing side reactions or complete failure of the reaction cascade. |
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