1229041-75-1Relevant academic research and scientific papers
Total synthesis of (+)-Sieboldine a: Evolution of a pinacol-terminated cyclization strategy
Canham, Stephen M.,France, David J.,Overman, Larry E.
, p. 9 - 34 (2013/04/10)
This article describes synthetic studies that culminated in the first total synthesis of the Lycopodium alkaloid sieboldine A. During this study, a number of pinacolterminated cationic cyclizations were examined to form the cishydrindanone core of siebold
Total synthesis of (+)-sieboldine A
Canham, Stephen M.,France, David J.,Overman, Larry E.
supporting information; experimental part, p. 7876 - 7877 (2010/08/04)
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).
