- Total synthesis of (±)-cavicularin: Control of pyrone diels-alder regiochemistry using isomeric vinyl sulfones
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An intramolecular pyrone Diels-Alder reaction-elimination retro-Diels-Alder cascade of a vinyl sulfone was used in the synthesis of cavicularin, a molecule possessing conformational chirality. The vinyl sulfone substitution pattern allowed for regiocontrol in the Diels-Alder cascade event.
- Zhao, Peng,Beaudry, Christopher M.
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supporting information
p. 402 - 405
(2013/03/13)
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- NEODIHYDROTHEBAINE AND BRACTAZONINE, TWO DIBENZAZONINE ALKALOIDS OF PAPAVER BRACTEATUM
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Two new dibenzazonine alkaloids, neodihydrothebaine and bractazonine were isolated from Papaver bracteatum.Their possible biosynthesis from thebaine is discussed.The structures of both new alkaloids are proven by synthesis.An isomeric dibenzazonine compound was also prepared. - Keywords: Papaver bracteatum; Papaveraceae; alkaloids; dibenzazonines; neodihydrothebaine; bractazonine; biosynthetic pathway; synthesis; 5,6,8,9-tetrahydro-2-methoxy-7-methyl-dibenzazonin-1,12-diol; 5,6,8,9-tetrahydro-2,10-dimethoxy-7-methyl-dibenzazonin-1-ol; 5,6,8,9-tetrahydro-2,11-dimethoxy-7-methyl-dibenz-azonin-1-ol; 5,6,8,9-tetrahydro-2,12-dimethoxy-7-methyl-dibenzazonin-1-ol.
- Theuns, Hubert G.,Lenting, Herman B. M.,Salemink, Cornelis A.,Tanaka, Hitoshi,Shibata, Masayoshi,et al.
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p. 1157 - 1166
(2007/10/02)
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