Journal
TETRAHEDRON LETTERS
Volume 51, Issue 15, Pages 1945-1946Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2010.01.101
Keywords
Cryptocaryone; Chiral auxiliary; Intramolecular bromoetherification; CAN
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Funding
- Japan Society for the Promotion of Science
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The first asymmetric total syntheses of the (+)- and (-)-cryptocaryones are described. Removal of the acetal unit of the enone acetal 5, which was obtained in our previous study from the cyclohexadiene acetal 3, afforded the enone acetal 8 in a one-pot procedure. The acylation of 8 with cinnamoyl chloride and subsequent hydrolysis of the resulting acetal gave the lactol 11. Its oxidation with NIS and tetra-n-butyl-ammonium iodide (TBAI) finally furnished the natural (+)-cryptocaryone 2. The same procedure from ent-3 afforded the unnatural one 1. (C) 2010 Elsevier Ltd. All rights reserved.
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