Total synthesis of pyripyropene A

Total synthesis of pyripyropene A

The total synthesis of pyripyropene A, a potent ACAT2 inhibitor with high isozyme selectivity, was completed. Key features of the synthetic strategy include Ti(III)-mediated radical cyclization and Peterson olefination for the construction of the AB ring segment and stereoselective dihydro-γ-pyrone...

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Veröffentlicht in:Tetrahedron 2011-10, Vol.67 (42), p.8195-8203
Hauptverfasser: Odani, Atsuki, Ishihara, Kaoru, Ohtawa, Masaki, Tomoda, Hiroshi, Omura, Satoshi, Nagamitsu, Tohru
Format: Artikel
Sprache:eng
Schlagworte:
ACAT2 inhibitor
Chemistry
Construction
Exact sciences and technology
Formations
Free radicals chemistry
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Inhibitors
Organic chemistry
Preparations and properties
Pyripyropene A
Radicals
Reactivity and mechanisms
Segments
Strategy
Synthesis (chemistry)
Tetrahedrons
Total synthesis
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Zusammenfassung:The total synthesis of pyripyropene A, a potent ACAT2 inhibitor with high isozyme selectivity, was completed. Key features of the synthetic strategy include Ti(III)-mediated radical cyclization and Peterson olefination for the construction of the AB ring segment and stereoselective dihydro-γ-pyrone formation (C-ring). The total synthesis provided pyripyropene A in 5.3% overall yield over 17 steps. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2011.06.084