Studies on the synthesis of landomycin A. Synthesis of the originally assigned structure of the aglycone, landomycinone, and revision of structure.
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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DOI：
10.1002/chin.200448187
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发表时间：
2004-06
期刊：
影响因子：
--
通讯作者：
William R. Roush;R. Jeffrey Neitz
中科院分区：
文献类型：
--
作者：
William R. Roush;R. Jeffrey Neitz
兰霉素酮（兰霉素 A 的苷元）最初提出的结构 (2) 已被合成，并显示与天然衍生的兰霉素 A 苷元不同。 2的合成以铬卡宾5和炔6的Dötz苯环化反应以及酚萘醌20的分子内迈克尔型环化反应为特征。有人提出天然兰多西酮具有替代结构3，但通过异构酚萘醌38的迈克尔型环化获得该结构的尝试尚未成功。
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 Dötz 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.