Total synthesis of (+/-)-alantrypinone by hetero Diels-Alder reaction |
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Authors: | Chen Zecheng Fan Junfa Kende Andrew S |
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Affiliation: | Department of Chemistry, University of Rochester, Rochester, New York 14627, USA. |
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Abstract: | An efficient total synthesis of (+/-)-alantrypinone 4 by hetero Diels-Alder reaction of a novel pyrazine diene 9 with either a functionalized 3-alkylideneoxindole or 3-methyleneoxindole itself is described. The Diels-Alder reactions provide both the desired regiochemistry and exo selectivity. An interesting anionic equilibration between alantrypinone 4 and its epimer 31 or between its ester analogues 23 and 24 has been demonstrated, and a mechanism has been proposed. |
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