Practical asymmetric synthesis of a selective endothelin A receptor (ETA) antagonist

Zhiguo J. Song, Matthew Zhao, Lisa Frey, Jing Li, Lushi Tan, Cheng Y. Chen, David M. Tschaen, Richard Tillyer, Edward J.J. Grabowski, Ralph Volante, Paul J. Reider, Yoshiaki Kato, Shigemitsu Okada, Takayuki Nemoto, Hiroki Sato, Atsushi Akao, Toshiaki Mase

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Abstract

Equation presented A practical, chromotography-free asymmetric synthesis was developed for the large scale preparation of an endothelin receptor antagonist 2. This synthesis includes a new efficient process for the preparation of 6-bromo-2,3-dihydrobenzofuran, a stereoselective conjugate addition of an aryllithium followed by stereospecific addition of the Grignard reagent of the top aryl bromide, and an aminophosphate-mediated sterospecific intramolecular enolate alkylation, which led to the formation of the five-membered ring bearing three contiguous asymmetric centers.

Original languageEnglish (US)
Pages (from-to)3357-3360
Number of pages4
JournalOrganic Letters
Volume3
Issue number21
DOIs
StatePublished - Oct 18 2001
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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    Song, Z. J., Zhao, M., Frey, L., Li, J., Tan, L., Chen, C. Y., Tschaen, D. M., Tillyer, R., Grabowski, E. J. J., Volante, R., Reider, P. J., Kato, Y., Okada, S., Nemoto, T., Sato, H., Akao, A., & Mase, T. (2001). Practical asymmetric synthesis of a selective endothelin A receptor (ETA) antagonist. Organic Letters, 3(21), 3357-3360. https://doi.org/10.1021/ol016601s