4.4 Article

Total synthesis of aculeatins A and B via a tethered oxa-Michael approach

Journal

TETRAHEDRON LETTERS
Volume 48, Issue 27, Pages 4683-4685

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2007.05.026

Keywords

aculeatin; marouka allylation; oxa-michael reaction; spirocyclic natural products

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A stereocontrolled total synthesis of aculeatins A and B has been achieved in eight steps and in 15% overall yield. The key feature of this synthetic approach is the application of a Marouka allylation and tethered intrarmolecular oxa-Michael reaction to install the required stereocentres on the tetrahydropyran ring. (c) 2007 Elsevier Ltd. All rights reserved.

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