Triethysilyl Enol Ethers in the Synthesis of Carbapenem Precursors

Thu Q Nguyen; Weirui Chai; Jane Gu; Katie Cook; Eugene Kim; Sam Goetz; Zach Farni; Monica Chepuru; Melina Cox; Pauline Nguyen; Hashim Raja; Patrick Magistrado; Faith Michael; Peter Oelschlaeger; John D Buynak

doi:10.1016/j.tetlet.2015.01.025

Triethysilyl Enol Ethers in the Synthesis of Carbapenem Precursors

Tetrahedron Lett. 2015 Jun 3;56(23):3385-3389. doi: 10.1016/j.tetlet.2015.01.025.

Authors

Affiliations

¹ Department of Chemistry, Southern Methodist University, Dallas, TX 75275.
² Hockaday School, 11600 Welch Rd, Dallas, TX 75229.
³ University of Texas at Austin, Austin, TX 78712.
⁴ Plano West Senior High School, 5601 W. Parker Rd, Plano, TX 75093.
⁵ Department of Pharmaceutic Sciences, Western University of Health Sciences, Pomona, CA 91766.
⁶ Department of Chemistry, Southern Methodist University, Dallas, TX 75275 ; Center for Drug Discovery, Design, and Delivery, Dedman College, Southern Methodist University, Dallas, TX 75275.

Abstract

A diastereoselective process for the formation of intermediates suitable for the preparation of C1 substituted carbapenems was developed. The process is readily scalable and does not involve organometallics or strong bases such as LDA.

Keywords: Antibiotic; Carbapenem; Lewis acid; silyl enol ether; β-Lactam.

Abstract

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