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Synlett 1999; 1999(10): 1612-1614
DOI: 10.1055/s-1999-2912
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An Unprecedented Asymmetric Nazarov Cyclization for the Synthesis of Nonracemic Indanes as Endothelin Receptor Antagonists

Lendon N. Pridgen* , Kris Huang, Susan Shilcrat, Ann Tickner-Eldridge, Charles DeBrosse, R. Curtis Haltiwanger
  • *SmithKline Beecham Pharmaceuticals, Synthetic Chemistry Department, 709 Swedeland Rd, King of Prussia, Pennsylvania, 19406, USA
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Publication Date:
31 December 1999 (online)

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An asymmetric synthesis of the novel nonracemic endothelin receptor antagonists, SB 209670 (1 a) and SB 217242 (1 b) is described which utilizes an unprecedented asymmetric Nazarov-type ring closure of the alkylidene-1,3-carbonyl compounds. Excellent 1,5-induction is observed which establishes the required S configuration at the C-3 carbon of an indane skeleton.

asymmetric Nazarov cyclization - 1,5-asymmetric induction - endothelin receptor antagonists - indanes