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Shemet A, Carreira EM. Total Synthesis of (-)-Rhazinilam and Formal Synthesis of (+)-Eburenine and (+)-Aspidospermidine: Asymmetric Cu-Catalyzed Propargylic Substitution. Org Lett. 2017;19(20):5529-5532doi: 10.1021/acs.orglett.7b02619.
Shemet, A., & Carreira, E. M. (2017). Total Synthesis of (-)-Rhazinilam and Formal Synthesis of (+)-Eburenine and (+)-Aspidospermidine: Asymmetric Cu-Catalyzed Propargylic Substitution. Organic letters, 19(20), 5529-5532. https://doi.org/10.1021/acs.orglett.7b02619
Shemet, Andrej, and Carreira, Erick M. "Total Synthesis of (-)-Rhazinilam and Formal Synthesis of (+)-Eburenine and (+)-Aspidospermidine: Asymmetric Cu-Catalyzed Propargylic Substitution." Organic letters vol. 19,20 (2017): 5529-5532. doi: https://doi.org/10.1021/acs.orglett.7b02619
Shemet A, Carreira EM. Total Synthesis of (-)-Rhazinilam and Formal Synthesis of (+)-Eburenine and (+)-Aspidospermidine: Asymmetric Cu-Catalyzed Propargylic Substitution. Org Lett. 2017 Oct 20;19(20):5529-5532. doi: 10.1021/acs.orglett.7b02619. Epub 2017 Oct 02. PMID: 28968107.
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Org Lett. 2017 Oct 20;19(20):5529-5532. doi: 10.1021/acs.orglett.7b02619. Epub 2017 Oct 02.

Total Synthesis of (-)-Rhazinilam and Formal Synthesis of (+)-Eburenine and (+)-Aspidospermidine: Asymmetric Cu-Catalyzed Propargylic Substitution.

Organic letters

Andrej Shemet, Erick M Carreira

Affiliations

  1. ETH Zürich , Vladimir-Prelog-Weg 3, 8093 Zürich, Switzerland.

PMID: 28968107 DOI: 10.1021/acs.orglett.7b02619

Abstract

A total synthesis of (-)-rhazinilam and formal syntheses of (+)-eburenine and (+)-aspidospermidine that rely on a copper(I)-catalyzed asymmetric propargylic substitution as the key step are reported. A salient feature of the reaction is the asymmetric construction of a quaternary stereocenter in high yield and enantiomeric excess.

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