Synthesis of Novel HMG‐CoA Reductase Inhibitors, I. Naphthalene Analogs of Mevinolin

L. Novák, JáNos Rohály, L. Poppe, Gábor Hornyánszky, P. Kolonits, István Zelei, Imre Fehér, J. Fekete, Éva Szabó, Uwe Záhorszky, András Jávor, Csaba Szántay

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Abstract

The title compounds 2 and their corresponding (6 S) epimers 18 are prepared in several steps by starting with chiral formyl ester 5, and α‐tetralones 10: (1) coupling reaction with the ylide generated from 11 to yield unsaturated ester 13, (2) reduction to the corresponding alcohol 14, (3) addition of the Grignard reagent derived from 14 to formyl ester 5 to afford the hydroxy esters 16 and 17, and (4) lactonization. This procedure is also used to synthesize the β‐naphthyl analogs 29 and 30. Some results obtained from HMG‐CoA reductase inhibitor screening are also reported.

Original languageEnglish
Pages (from-to)145-157
Number of pages13
JournalLiebigs Annalen der Chemie
Volume1992
Issue number2
DOIs
Publication statusPublished - 1992

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Keywords

  • Glutarate, 3‐hydroxy
  • HMG‐CoA reductase inhibitors
  • Lactones
  • Naphthylacetates
  • Pig liver esterase

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Novák, L., Rohály, J., Poppe, L., Hornyánszky, G., Kolonits, P., Zelei, I., Fehér, I., Fekete, J., Szabó, É., Záhorszky, U., Jávor, A., & Szántay, C. (1992). Synthesis of Novel HMG‐CoA Reductase Inhibitors, I. Naphthalene Analogs of Mevinolin. Liebigs Annalen der Chemie, 1992(2), 145-157. https://doi.org/10.1002/jlac.199219920127