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Synthesis 2010(15): 2567-2570  
DOI: 10.1055/s-0029-1218822
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© Georg Thieme Verlag Stuttgart ˙ New York

Total Synthesis of (±)-Batzelladine K: A Biomimetic Approach

Nafees Ahmed, Keyur G. Brahmbhatt, Inder Pal Singh, Kamlesh K. Bhutani*
Department of Natural Products, National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, S. A. S. Nagar, Mohali, Punjab 160062, India
Fax: +91(172)2232208; e-Mail: kkbhutani@niper.ac.in;
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Publication History

Received 29 March 2010
Publication Date:
17 June 2010 (online)

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Abstract

Total synthesis of batzelladine K was achieved by a biomimetic approach. The key reactions involve two Wittig reactions of phosphoranes and aldehydes leading to an α,β-unsaturated ketone, followed by a condensation with guanidine. The synthesis was accomplished in four steps with an overall yield of 12%. The relative stereochemistry of batzelladine K was established by NOE experiments and comparison with literature values.

Key words

batzelladines - marine natural products - tricyclic guanidine - phosphorane - biomimetic synthesis