Chromium-mediated asymmetric synthesis of both enantiomers of acetoxytubipofuran |
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Authors: | Kündig E Peter Cannas Rita Laxmisha Mundruppady Ronggang Liu Tchertchian Sylvie |
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Affiliation: | Department of Organic Chemistry, University of Geneva, 30 Quai Ernest Ansermet, 1211 Geneva 4, Switzerland. peter.kundig@chiorg.unige.ch |
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Abstract: | Both enantiomers of acetoxytubipofuran were synthesized using enantioselective and diastereoselective dearomatization sequences starting from the benzaldehyde chromium tricarbonyl complex. Following aldol condensation, a sequence involving Pd-catalyzed allylic substitution was used in the synthesis of the (-)-enantiomer, whereas the (+)-enantiomer was reached via an Eschenmoser-Claisen rearrangement. Chiroptical data show that a revision of the previously assigned absolute configuration of the natural product is required. |
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