4.4 Article

Enantioselective synthesis and absolute configurations of aculeatins A and B

Journal

TETRAHEDRON LETTERS
Volume 46, Issue 48, Pages 8407-8410

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2005.09.146

Keywords

aculeatins; enantioselective synthesis; phenol oxidation; aldol reaction; asymmetric allylation

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The two naturally occuring, bioactive spiroacetals aculeatins A and B have been synthesized for the first time in enantiopure form using an asymmetric allylation as the only chirality source. A further key step was a stereoselective aldol reaction with remote induction. The absolute configurations of the natural products have been established and the previously assigned relative configurations have been corrected. (c) 2005 Elsevier Ltd. All rights reserved.

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