The Revised Structure, Total Synthesis, and Absolute Configuration of Streptophenazine A

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• 作者：Zhicai Yang ; Xiaomin Jin ; Michael Guaciaro ; Bruce F. Molino ; Ursula Mocek ; Ricardo Reategui ; Joshua Rhea ; Tim Morley
• 刊名：Organic Letters
• 出版年：2011
• 出版时间：October 21, 2011
• 年：2011
• 卷：13
• 期：20
• 页码：5436-5439
• 全文大小：787K
• 年卷期：v.13,no.20(October 21, 2011)
• ISSN：1523-7052

文摘

A total synthesis of both diastereomers of the originally proposed structure for streptophenazine A (1) has been achieved. However, both synthetic compounds are different from the natural product. Re-examination of NMR data reported for streptophenazine A and a concise total synthesis of both diastereomers of 17 (17a and 17b) led to the structural revision of streptophenazine A to 17b. Asymmetric synthesis of (鈭?-streptophenazine A was also conducted, and its absolute configuration was determined to be 1鈥?i>S,2鈥?i>R.