Enantiocontrolled Total Syntheses of Breviones A, B, and C

Enantiocontrolled Total Syntheses of Breviones A, B, and C

Enantiocontrolled total syntheses of the breviones A, B, and C have been accomplished using a highly diastereoselective oxidative coupling of an α-pyrone with a tricyclic diene prepared from an optically pure Wieland–Miescher ketone derivative through the 7-endo-trig mode of acyl radical cyclization...

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Veröffentlicht in:Journal of the American Chemical Society 2011-06, Vol.133 (23), p.8854-8857
Hauptverfasser: Yokoe, Hiromasa, Mitsuhashi, Chika, Matsuoka, Yoko, Yoshimura, Tomoyuki, Yoshida, Masahiro, Shishido, Kozo
Format: Artikel
Sprache:eng
Schlagworte:
Cyclization
Diterpenes - chemical synthesis
Diterpenes - chemistry
Polycyclic Compounds - chemical synthesis
Polycyclic Compounds - chemistry
Pyrones - chemical synthesis
Pyrones - chemistry
Spiro Compounds - chemical synthesis
Spiro Compounds - chemistry
Stereoisomerism
Substrate Specificity
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Zusammenfassung:Enantiocontrolled total syntheses of the breviones A, B, and C have been accomplished using a highly diastereoselective oxidative coupling of an α-pyrone with a tricyclic diene prepared from an optically pure Wieland–Miescher ketone derivative through the 7-endo-trig mode of acyl radical cyclization.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja202874d