Organometallation of (R)-2,3-cyclohexylideneglyceraldehyde derived ketones: a simple and stereoselective strategy for the synthesis of (+)-tanikolide

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Abstract

Several metal mediated allylations and Grignard additions to ketones 3 and 5, both derived from (R)-2,3-cylcohexylideneglyceraldehyde, took place with very high diastereoselectivity producing the same tertiary carbinol 4b as the major product. Subsequently, 4b was exploited to synthesize (+)-tanikolide efficiently through a series of simple reactions employing an RCM strategy. © 2008 Elsevier Ltd. All rights reserved.

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Vichare, P., & Chattopadhyay, A. (2008). Organometallation of (R)-2,3-cyclohexylideneglyceraldehyde derived ketones: a simple and stereoselective strategy for the synthesis of (+)-tanikolide. Tetrahedron Asymmetry, 19(5), 598–602. https://doi.org/10.1016/j.tetasy.2008.01.034

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