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
复制标题
DOI：
10.1021/jo049426c
复制
发表时间：
2004-07-23
影响因子：
3.6
通讯作者：
Neitz, RJ
中科院分区：
文献类型：
--
作者：
Roush, WR;Neitz, RJ
最初提出的landomycinone（landomycin A的糖苷配基）结构（2）已被合成，并显示与天然衍生的landomycin A糖苷配基不同。2的合成特征在于铬卡宾5和炔6的Dotz苯并环化反应，以及酚萘醌20的分子内Michael型环化反应。有人提出，天然兰霉素酮具有替代结构3，但试图通过迈克尔型环化的异构体酚萘醌38获得这种结构是不成功的。
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 Dotz 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.