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Enantioselective syntheses of candenatenins B and C using a chiral anthracene auxiliary

✍ Scribed by Amanda L. Jones; Xiang Liu; John K. Snyder

Book ID: 104097306
Publisher: Elsevier Science
Year: 2010
Tongue: French
Weight: 584 KB
Volume: 51
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2009.12.108

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✦ Synopsis

The asymmetric syntheses of two anticancer natural products, candenatenins B and C, are described, leading to a revision of the originally assigned stereochemistries. The syntheses follow a Diels-Alder/ retro-Diels Alder strategy using a chiral anthracene auxiliary to access both targets with 90% ee. The inherent structural qualities of the auxiliary allow for both regio-and diastereoselective transformations.

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