Total synthesis of (+)-sieboldine A
Journal of the American Chemical Society, ISSN: 0002-7863, Vol: 132, Issue: 23, Page: 7876-7877
2010
- 93Citations
- 72Captures
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Metrics Details
- Citations93
- Citation Indexes93
- CrossRef93
- 82
- Captures72
- Readers72
- 72
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.
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