Establishment of Relative and Absolute Configurations of Phaeosphaeride A: Total Synthesis of ent-Phaeosphaeride A
Установление относительной и абсолютной конфигураций феосфаеридина A: тотальный синтез ent‑феосфаеридина A
2014-12-17
SCID: 54.1/h643d6hz
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Sharpless asymmetric dihydroxylationent-phaeosphaeride Aintramolecular vinyl anion aldol reactionphaeosphaeride Atotal synthesis
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Abstract (AI)
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.
Key Findings
1
The first total synthesis of ent-phaeosphaeride A was achieved, enabling structural assignment.
2
The relative and absolute configurations of phaeosphaeride A were established through this synthesis.
3
The total synthesis led to revision of the originally proposed structure of natural phaeosphaeride A.
4
Three contiguous stereogenic centers were installed using Sharpless asymmetric dihydroxylation and a stereoselective intramolecular vinyl anion aldol reaction.
Research Object
phaeosphaeride A (natural product) and its synthetic enantiomer ent-phaeosphaeride A
Research Subject
establishment of the relative and absolute stereochemical configurations via total synthesis, including installation of three contiguous stereogenic centers using Sharpless asymmetric dihydroxylation and a stereoselective intramolecular vinyl anion aldol reaction
Publication Details
Publication Date
2014-12-17
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