Synthesis of (-)-xialenon A by enantioselective alpha-deprotonation-rearrangement of a meso-epoxide
- The first total synthesis of (-)-xialenon A was achieved via enantioselective transannular desymmetrisation of a substituted cycloctene oxide using an organolithium/(-)-α-isosparteine combination. Oxidation of the resulting bicyclo[3.3.0]octanol gave an enone which underwent stereoselective conjugate allylation; subsequent α′-hydroxylation on the more hindered face of a derived enone using hypervalent iodine chemistry led to the natural product. © 2003 Elsevier Ltd. All rights reserved.
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