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Total synthesis of (+)-sieboldine A

Journal of the American Chemical Society, ISSN: 0002-7863, Vol: 132, Issue: 23, Page: 7876-7877
2010
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Article Description

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). © 2010 American Chemical Society.

Bibliographic Details

Stephen M. Canham; David J. France; Larry E. Overman

American Chemical Society (ACS)

Chemical Engineering; Chemistry; Biochemistry, Genetics and Molecular Biology

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