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Hethcox JC, Shanahan CS, Martin SF. Total synthesis of (-)-dihydroprotolichesterenic acid via diastereoselective conjugate addition to chiral fumarates. Tetrahedron Lett. 2013;54(16):2074-2076doi: 10.1016/j.tetlet.2013.02.014.
Hethcox, J. C., Shanahan, C. S., & Martin, S. F. (2013). Total synthesis of (-)-dihydroprotolichesterenic acid via diastereoselective conjugate addition to chiral fumarates. Tetrahedron letters, 54(16), 2074-2076. https://doi.org/10.1016/j.tetlet.2013.02.014
Hethcox, J Caleb, et al. "Total synthesis of (-)-dihydroprotolichesterenic acid via diastereoselective conjugate addition to chiral fumarates." Tetrahedron letters vol. 54,16 (2013): 2074-2076. doi: https://doi.org/10.1016/j.tetlet.2013.02.014
Hethcox JC, Shanahan CS, Martin SF. Total synthesis of (-)-dihydroprotolichesterenic acid via diastereoselective conjugate addition to chiral fumarates. Tetrahedron Lett. 2013 Apr 17;54(16):2074-2076. doi: 10.1016/j.tetlet.2013.02.014. Epub 2013 Feb 11. PMID: 23539490; PMCID: PMC3607549.
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Tetrahedron Lett. 2013 Apr 17;54(16):2074-2076. doi: 10.1016/j.tetlet.2013.02.014. Epub 2013 Feb 11.

Total synthesis of (-)-dihydroprotolichesterenic acid via diastereoselective conjugate addition to chiral fumarates.

Tetrahedron letters

J Caleb Hethcox, Charles S Shanahan, Stephen F Martin

Affiliations

  1. Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, Texas 78712.

PMID: 23539490 PMCID: PMC3607549 DOI: 10.1016/j.tetlet.2013.02.014

Abstract

A diastereoselective conjugate addition of a variety of monoorganocuprates, Li[RCuI], to chiral fumarates to provide funtionalized succinates has been developed. The utility of this reaction is demonstrated in a concise total synthesis of (-)-dihydroprotolichesterenic acid that required only four steps and proceeded in an overall 31% yield.

Keywords: Butyrolactone; Chiral Auxiliary; Conjugate addition; Succinate; Total Synthesis

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