Stereoselective Total Synthesis of the Putative Structure of Nitraraine

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• 作者：Federica Arioli ; Maria P茅rez ; Fabiana Subrizi ; N煤ria Llor ; Joan Bosch ; Mercedes Amat
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：August 15, 2014
• 年：2014
• 卷：79
• 期：16
• 页码：7740-7745
• 全文大小：294K
• ISSN：1520-6904

文摘

After the structure originally proposed for nitraraine was shown to be incorrect by total synthesis, the alternative structure 5 was recently suggested for the alkaloid on biosynthetic grounds and by comparison with the ¹H NMR data of tangutorine. The unambiguous synthesis of 5 is reported from tryptophanol and ketodiester 6, via oxazoloquinolone lactam 7. However, the melting point and ¹H NMR data of 5 did not match those reported for the natural product.