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Synfacts 2006(10): 0976-0976  
DOI: 10.1055/s-2006-949317
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 1-Cytosinyl-N-malayamycin A

Contributor(s): Philip Kocienski
O. Loiseleur*, H. Schneider, G. Huang, R. Machaalani, P. Sellès, P. Crowley, S. Hanessian*
Syngenta Crop Protection AG, Basel, Switzerland
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Publication History

Publication Date:
21 September 2006 (online)

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Significance

The target antifungal molecule is an equipotent 1-cytosinyl analogue of natural Malayamycin A, its 3-cytosinyl congener. The synthesis relies solely on substrate control to introduce all six contiguous stereogenic centers. The key steps are (a) the ring-closing metathesis (RCM) reaction used to create the bicycle B and (b) the N-nucleosidation via activation of the O,S-acetal F.