Total synthesis of cyclosporin O by convergent approach employing Fmoc-amino acid chlorides mediated by zinc dust.

Subramanyam J Tantry, Rao Venkataramanarao, Gundala Chennakrishnareddy, Vommina Venkata Sureshbabu

Department of Studies in Chemistry, Central College Campus, Bangalore University, Bangalore, India.

The Journal of organic chemistry 2007 Nov 23

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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. The couplings were performed by employing Fmoc-amino acid chlorides and were mediated by zinc dust under neutral conditions. The yield and purity of the coupling of sterically hindered N-methylamino acids to N-methylamino acids at positions 8, 9, 10, and 11 were enhanced by repeating the coupling thrice at these particular junctures. All the 10 intermediate peptides pertaining to CsO and the final CsO were isolated and completely characterized through IR, 1H NMR, mass spectrometry, and HPLC techniques.

Citation

Subramanyam J Tantry, Rao Venkataramanarao, Gundala Chennakrishnareddy, Vommina Venkata Sureshbabu. Total synthesis of cyclosporin O by convergent approach employing Fmoc-amino acid chlorides mediated by zinc dust. The Journal of organic chemistry. 2007 Nov 23;72(24):9360-3