Syntheses of (−)-Tatarinoid A, (±)-Tatarinoid B, and (−)-Tatarinoid C

Yuriy Slutskyy; William T Jewell; Claudia G Lucero

doi:10.1016/j.tetlet.2012.10.104

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Syntheses of (−)-Tatarinoid A, (±)-Tatarinoid B, and (−)-Tatarinoid C

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Syntheses of (−)-Tatarinoid A, (±)-Tatarinoid B, and (−)-Tatarinoid C

Yuriy Slutskyy, William T Jewell and Claudia G Lucero

Tetrahedron letters, Vol.54(3), pp.210-212

01/16/2013

DOI: https://doi.org/10.1016/j.tetlet.2012.10.104

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https://hdl.handle.net/20.500.12741/rep:3563

Abstract

(−)-Tatarinoid A

(±)-Tatarinoid B

(−)-Tatarinoid C

Irregular Wittig reaction

Crossed acyloin condensation

The syntheses of (−)-Tatarinoid A, (±)-Tatarinoid B, and (−)-Tatarinoid C in one to three steps are described herein. (−)-Tatarinoid A and (−)-Tatarinoid C are both constructed in three steps from 1-bromo-2,4,5-trimethoxybenzene in overall yields of 63% and 74%, respectively. The addition of (1-methoxyethyl)triphenylphosphonium ylide to 2,4,5-trimethoxybenzaldehyde provides (±)-Tatarinoid B in one step in 97% yield.

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Title: Syntheses of (−)-Tatarinoid A, (±)-Tatarinoid B, and (−)-Tatarinoid C
Creators: Yuriy Slutskyy - Department of Chemistry, California State University, Sacramento, 6000 J Street, Sacramento, CA 95819, USA
William T Jewell - University of California, Davis, One Shields Ave., Davis, CA 95616, USA
Claudia G Lucero - Department of Chemistry, California State University, Sacramento, 6000 J Street, Sacramento, CA 95819, USA
Academic Unit: Chemistry Department
Publisher: Elsevier Ltd
Publication Details: 01/16/2013
Identifiers: 99257847580601671; https://hdl.handle.net/20.500.12741/rep:3563; https://doi.org/10.1016/j.tetlet.2012.10.104
Language: English

Syntheses of (−)-Tatarinoid A, (±)-Tatarinoid B, and (−)-Tatarinoid C

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