An interesting issue of Diels-Alder selectivity discovered en route to 11-O-debenzoyltashironin |
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Authors: | Cook Silas P 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: | The hypervalent iodine-mediated oxidative dearomatization/Diels-Alder cascade was examined in the context of the natural product 11-O-debenzoyltashironin. Interestingly, the regioselectivity of the Diels-Alder reaction can be completely switched by changing the dienophile. Trapping of allyl alcohols during the oxidative dearomatization gives rise to the five-membered acetal, while trapping of allenyl alcohols results in the six-membered acetal. reaction: see text] |
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