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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Publisher's URL: http://dx.doi.org/10.1021/jo300872y
Abstract
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 |
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Status: | Published |
Refereed: | Yes |
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: | 0022-3263 |
ISSN (Online): | 1520-6904 |
Published Online: | 26 June 2012 |
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