Total Synthesis of Amphidinolide F

Total Synthesis of Amphidinolide F

Orchestrated yet nonconsonant: The challenge posed by the “umpoled” 1,4‐dioxygenation pattern characteristic for the polyketide frame of amphidinolide F was mastered by a late‐stage ring‐closing alkyne metathesis followed by a directed transannular hydration under the aegis of a carbophilic π‐acid c...

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Veröffentlicht in:Angewandte Chemie International Edition 2013-09, Vol.52 (36), p.9534-9538
Hauptverfasser: Valot, Gaëlle, Regens, Christopher S., O'Malley, Daniel P., Godineau, Edouard, Takikawa, Hiroshi, Fürstner, Alois
Format: Artikel
Sprache:eng
Schlagworte:
alkyne metathesis
Macrolides - chemical synthesis
Macrolides - chemistry
Molecular Structure
molybdenum
natural products
platinum
total synthesis
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Zusammenfassung:Orchestrated yet nonconsonant: The challenge posed by the “umpoled” 1,4‐dioxygenation pattern characteristic for the polyketide frame of amphidinolide F was mastered by a late‐stage ring‐closing alkyne metathesis followed by a directed transannular hydration under the aegis of a carbophilic π‐acid catalyst. This concordant strategy enabled a concise total synthesis of this enticing marine natural product.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201301700