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Synfacts 2006(4): 0304-0304  
DOI: 10.1055/s-2006-932036
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (-)-Scabronine G

Contributor(s): Philip Kocienski, Thomas Snaddon
S. P. Waters, Y. Tian, Y.-M. Li, S. J. Danishefsky*
Sloan-Kettering Institute for Cancer Research and Columbia University, New York, USA
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Publication History

Publication Date:
24 March 2006 (online)

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Significance

Danishefsky and co-workers have disclosed a concise and efficient synthesis of the nerve growth factor Scabronine G from the Wieland-Miescher ketone. This synthesis makes elegant use of classical chemistry and fully exploits substrate control. Of particular note is the two-step carbocyclic ring expansion of n-propyl­thiomethylene cyclohexanone A to formyl cycloheptenone I via the procedure of Guerrero et al. (Tetrahedron Lett. 1990, 31, 1873-1876).