4.8 Article

Concise, stereoselective approach to the spirooxindole ring system of citrinadin A

Journal

ORGANIC LETTERS
Volume 9, Issue 22, Pages 4623-4626

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol702132v

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Funding

  1. NIGMS NIH HHS [GM 25439] Funding Source: Medline

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The spirooxindole ring system of citrinadin A has been synthesized with excellent control over the absolute stereochemistry at the spirocenter. The key step involves a novel diastereoselective DMDO-mediated oxidative rearrangement employing an 8-phenylmenthol chiral auxiliary on the indole nitrogen.

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