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American Chemical Society, Journal of the American Chemical Society, 23(132), p. 7876-7877, 2010

DOI: 10.1021/ja103666n

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Total Synthesis of (+)-Sieboldine A

Journal article published in 2010 by Stephen M. Canham ORCID, David J. France ORCID, Larry E. Overman
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This paper is available in a repository.

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Abstract

The first total synthesis of (+)-sieboldine A was completed in 20 steps from readily available (3aS,6aR)-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-2-one (5). Key steps are as follows: (a) a pinacol-terminated 1,6-enyne cyclization reaction to form the cis-hydrindanone core (11 --> 12), (b) formation of the spiro tetrahydrofuran ring by stereoselective DMDO oxidation of tricyclic dihydropyran intermediate 15, and (c) formation of the unprecedented N-hydroxyazacyclononane ring by cyclization of a thioglycoside precursor (18 --> 19).