Total Synthesis of Cyclosporin O by Convergent Approach Employing Fmoc-Amino Acid Chlorides Mediated by Zinc Dust

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• 作者：Subramanyam J Tantry ; Rao Venkataramanarao ; Gundala Chennakrishnareddy ; Vommina Venkata Sureshbabu
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：November 23, 2007
• 年：2007
• 卷：72
• 期：24
• 页码：9360 - 9363
• 全文大小：106K
• 年卷期：v.72,no.24(November 23, 2007)
• ISSN：1520-6904

文摘

jo701329wn00001>An epimerization free and efficient total synthesis of immunosuppressant cyclosporin O (CsO) by step-by-step assembly of amino acids in solution phase is reported. Thecouplings were performed by employing Fmoc-amino acidchlorides and were mediated by zinc dust under neutralconditions. The yield and purity of the coupling of stericallyhindered N-methylamino acids to N-methylamino acids atpositions 8, 9, 10, and 11 were enhanced by repeating thecoupling thrice at these particular junctures. All the 10intermediate peptides pertaining to CsO and the final CsOwere isolated and completely characterized through IR, ¹HNMR, mass spectrometry, and HPLC techniques.