Total synthesis of (+)-Sieboldine A: Evolution of a pinacol-terminated cyclization strategy

Canham, S.M., France, D.J. and Overman, L.E. (2013) Total synthesis of (+)-Sieboldine A: Evolution of a pinacol-terminated cyclization strategy. Journal of Organic Chemistry, 78(1), pp. 9-34. (doi: 10.1021/jo300872y)

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This article describes synthetic studies that culminated in the first total synthesis of the Lycopodium alkaloid sieboldine A. During this study, a number of pinacol-terminated cationic cyclizations were examined to form the cis-hydrindanone core of sieboldine A. Of these, a mild Au(I)-promoted 1,6-enyne cyclization that was terminated by a semipinacol rearrangement proved to be most efficient. Fashioning the unprecedented N-hydroxyazacyclononane ring embedded within the bicyclo[5.2.1]decane-N,O-acetal moiety of sieboldine A was a formidable challenge. Ultimately, the enantioselective total synthesis of (+)-sieboldine A was completed by forming this ring in good yield by cyclization of a protected-hydroxylamine thioglycoside precursor.

Item Type:Articles
Glasgow Author(s) Enlighten ID:France, Dr David
Authors: Canham, S.M., France, D.J., and Overman, L.E.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Journal of Organic Chemistry
Journal Abbr.:J. Org. Chem.
Publisher:American Chemical Society
ISSN (Online):1520-6904
Published Online:26 June 2012

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