Establishment of Relative and Absolute Configurations of Phaeosphaeride A: Total Synthesis of ent-Phaeosphaeride A

Establishment of Relative and Absolute Configurations of Phaeosphaeride A: Total Synthesis of ent-Phaeosphaeride A

The relative and absolute configurations of phaeosphaeride A have been established via the first total synthesis of ent-phaeosphaeride A. The three contiguous stereogenic centers were installed by Sharpless asymmetric dihydroxylation and a stereoselective intramolecular vinyl anion aldol reaction. T...

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Veröffentlicht in:Journal of organic chemistry 2015-01, Vol.80 (2), p.1243-1248
Hauptverfasser: Kobayashi, Kenichi, Kobayashi, Yukiko, Nakamura, Misato, Tamura, Osamu, Kogen, Hiroshi
Format: Artikel
Sprache:eng
Schlagworte:
Bridged Bicyclo Compounds, Heterocyclic - chemical synthesis
Bridged Bicyclo Compounds, Heterocyclic - chemistry
Hydroxylation
Molecular Structure
Stereoisomerism
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Zusammenfassung:The relative and absolute configurations of phaeosphaeride A have been established via the first total synthesis of ent-phaeosphaeride A. The three contiguous stereogenic centers were installed by Sharpless asymmetric dihydroxylation and a stereoselective intramolecular vinyl anion aldol reaction. This synthesis has altered the originally proposed structure of natural phaeosphaeride A.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo5025046