Journal
TETRAHEDRON LETTERS
Volume 49, Issue 41, Pages 5906-5908Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2008.07.139
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Funding
- National Institutes of Health [HL25848]
- Coumbia University [CHE-0619638]
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The mechanism of the cascade oxidative dearomatization-transannular Diels-Alder was investigated in the context of an asymmetric route to (-)-11-O-debenzoyltashironin. Although the oxidative dearomatization provides two acetal intermediates, the transannular Diels-Alder proceeds spontaneously from only one of the acetal isomers. Access to enantioenriched tetracyclic adduct was gained through the use of optically active allene. (C) 2008 Elsevier Ltd. All rights reserved.
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