Studies on the synthesis of landomycin A. Synthesis of the originally assigned structure of the aglycone, landomycinone, and revision of structure |
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Authors: | Roush William R Neitz R Jeffrey |
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Affiliation: | Department of Chemistry, University of Michigan, Ann Arbor, MI 48109, USA. roush@umich.edu |
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Abstract: | The originally proposed structure (2) of landomycinone, the aglycone of landomycin A, has been synthesized and shown to be nonidentical to the naturally derived landomycin A aglycone. The synthesis of 2 features the D?tz benzannulation reaction of chromium carbene 5 and alkyne 6, and the intramolecular Michael-type cyclization reaction of the phenolic naphthoquinone 20. It is proposed that natural landomycinone possesses the alternative structure 3, but attempts to access this structure via the Michael-type cyclization of the isomeric phenolic naphthoquinone 38 have been unsuccessful. |
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