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Chromium-Mediated Asymmetric Synthesis of Both Enantiomers of Acetoxytubipofuran

Laxmisha, M.
Ronggang, L.
Published in Journal of the American Chemical Society. 2003, vol. 125, no. 19, p. 5642-5643
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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KUNDIG, Ernst Peter et al. Chromium-Mediated Asymmetric Synthesis of Both Enantiomers of Acetoxytubipofuran. In: Journal of the American Chemical Society, 2003, vol. 125, n° 19, p. 5642-5643. doi: 10.1021/ja029957n https://archive-ouverte.unige.ch/unige:6986

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Deposited on : 2010-06-18

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