Journal
TETRAHEDRON
Volume 69, Issue 1, Pages 334-340Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2012.10.022
Keywords
Andavadoic acid; Cyclization; Endoperoxides; Hydroperoxysilylation; Plakortolides
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Funding
- French Ministere de la Recherche et de l'Enseignement Superieur
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The first total synthesis of andavadoic acid, a naturally occurring five-membered ring peroxide, and its absolute configuration assignment are reported. Central to this venture was the development of an effective synthesis of a key beta-hydroperoxy epoxy ester from (R)-epichlorohydrin via chemoselective methylenation with Nysted reagent in the presence of Ti(Oi-Pr)(2)Cl-2 and chemo- and regioselective Mukaiyama-Isayama peroxidation. This approach also featured the construction of the 1,2-dioxolane ring system by an efficient base-promoted 5-exo epoxide opening by a hydroperoxy group. (C) 2012 Elsevier Ltd. All rights reserved.
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