Enantioselective Total Synthesis of (−)- and (+)-Petrosin

Enantioselective Total Synthesis of (−)- and (+)-Petrosin

The enantioselective total synthesis of (−)- and (+)-petrosin is described. The union of two key segments was executed by Suzuki−Miyaura coupling. The quinolizidine rings were stereoselectively constructed via a diastereoselective Mannich reaction and an aza-Michael reaction. The 16-membered ring wa...

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Veröffentlicht in:Organic letters 2010-11, Vol.12 (22), p.5196-5199
Hauptverfasser: Toya, Hiroki, Okano, Kentaro, Takasu, Kiyosei, Ihara, Masataka, Takahashi, Atsushi, Tanaka, Haruo, Tokuyama, Hidetoshi
Format: Artikel
Sprache:eng
Schlagworte:
Alkaloids - chemical synthesis
Alkaloids - chemistry
Animals
Catalysis
Cyclization
Marine Biology
Molecular Structure
Petrosia - chemistry
Quinolizidines - chemical synthesis
Quinolizidines - chemistry
Stereoisomerism
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Zusammenfassung:The enantioselective total synthesis of (−)- and (+)-petrosin is described. The union of two key segments was executed by Suzuki−Miyaura coupling. The quinolizidine rings were stereoselectively constructed via a diastereoselective Mannich reaction and an aza-Michael reaction. The 16-membered ring was constructed by ring-closing metathesis with the second-generation Grubbs catalyst.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol1022257