TY - JOUR
T1 - Azomethine Ylide Cycloaddition Approach toward Dendrobine
T2 - Synthesis of 5-Deoxymubironine C
AU - Williams, Benjamin M.
AU - Trauner, Dirk
PY - 2018/3/16
Y1 - 2018/3/16
N2 - A concise route to the azatricyclo[6.2.1.04,11]undecane core of (-)-dendrobine and (-)-mubironine C is described wherein an unstabilized azomethine ylide cycloaddition provides the complete carbon framework of the natural products. The cyclization precursor is made in short order from (R)-carvone through an unconventional high-pressure Ireland-Claisen reaction. Attempts to install a final hydroxyl group through an intramolecular lactonization strategy and the observation of an unexpected and highly complex enal-ene product are also reported.
AB - A concise route to the azatricyclo[6.2.1.04,11]undecane core of (-)-dendrobine and (-)-mubironine C is described wherein an unstabilized azomethine ylide cycloaddition provides the complete carbon framework of the natural products. The cyclization precursor is made in short order from (R)-carvone through an unconventional high-pressure Ireland-Claisen reaction. Attempts to install a final hydroxyl group through an intramolecular lactonization strategy and the observation of an unexpected and highly complex enal-ene product are also reported.
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U2 - 10.1021/acs.joc.8b00192
DO - 10.1021/acs.joc.8b00192
M3 - Article
C2 - 29490142
AN - SCOPUS:85044060494
SN - 0022-3263
VL - 83
SP - 3061
EP - 3068
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 6
ER -