A total synthesis of xestodecalactone a and proof of its absolute stereochemistry: interesting observations on dienophilic control with 1,3-disubstituted nonequivalent allenes |
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| Authors: | Yoshino Toshiharu Ng Fay Danishefsky Samuel J |
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| Institution: | Department of Chemistry, Columbia University, Havemeyer Hall, 3000 Broadway, New York, NY 10027, USA. |
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| Abstract: | A concise total synthesis of xestodecalactone A, utilizing a Diels-Alder strategy is described. The focal Diels-Alder reaction relied on an "ynoate" dienophile to rapidly assemble the required resorcylinic acid scaffold. During this study, Diels-Alder cycloaddition reactions involving 1,3-disubstituted nonequivalent allene dienophiles were studied, and some surprising results were encountered. |
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