Convenient preparation of (Z)-α-halo-α,β-unsaturated aldehydes: synthesis of a Laurencia flexilis toxin |
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| Authors: | Deb K Barma Rachid Baati Charles Mioskowski |
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| Institution: | a Department of Biochemistry, University of Texas Southwestern Medical Center, Dallas, TX 75390, USA
b Université Louis Pasteur de Strasbourg, Faculté de Pharmacie UMR 7175-LC1, Laboratoire de Synthèse Bio-Organique, 74 route du Rhin, 67 401 Illkirch-Graffenstaden, France |
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| Abstract: | The CrCl2-mediated two-carbon halo-homologation of aryl, alkenyl, and aliphatic aldehydes with chloral ethyl hemiacetal or bromal affords (Z)-α-chloro- and (Z)-α-bromo-α,β-unsaturated aldehydes, respectively, in good to excellent yields and high stereoselectivity. The utility of this methodology was illustrated by a synthesis of 2-chloropentadec-2(Z)-enal, a toxin isolated from the marine red alga Laurencia flexilis. |
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| Keywords: | Homologation Chromium Aldehydes Enals |
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