New two-step sequence involving a hetero-Diels-Alder and a nonphenolic oxidative coupling reaction: a convergent access to analogs of steganacin |
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Authors: | Mathieu Y Laurent Vivien StockerValéry Momo Temgoua Gilles DujardinRobert Dhal |
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Institution: | UMR 6011 CNRS-Université du Maine, Laboratoire de Synthèse Organique (UCO2M), Avenue Olivier Messiaen, 72085 Le Mans Cedex 9, France |
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Abstract: | A new family of analogs of steganacin, an important antimitotic compound, was accessed. It takes advantage of a completely stereoselective sequence of two key steps. The central dihydropyrane core is built by a highly diastereoselective and facially controlled hetero-Diels-Alder reaction. It is followed by a nonphenolic biaryl oxidative coupling with a complete atropo-stereoselectivity. It leads to a quick way to form cyclic biaryl lignans. |
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Keywords: | Lignan Steganacin Hetero-Diels-Alder Biaryl coupling Atroposelectivity |
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