Synthesis of (S)-(+)-mevalonolactone and mevalonate analogues

Véronique Bolitt, Charles Mioskowski, R. K. Bhatt, J R Falck

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

Tetrahydropyran (R/S)-1, a vinylidene analogue of mevalonolactone, was prepared by addition of excess allyl Grignard to 4-acetoxy-2-butanone, iodoetherification of the resultant diol 5, and DBN-mediated dehydrohalogenation. Sharpless asymmetric epoxidation of 3-methylhexa-2,5-dien-1-ol (9) gave epoxide 10 that was reduced to diol 11 (>95% ee) by LiAlH4. Annulation and elimination of HI as described for 5 furnished (S)-1. Ozonolysis of (S)-1 yielded (S)-mevalonolactone (2), whereas bromomethoxylation and controlled hydrolysis led to 3, a reactive analogue of (S)-mevalonic acid. Analogue 4, a nonionizable lipophilic version of (S)-mevalonic acid, was generated upon exposure of (S)-1 or 2 to excess Tebbe-Grubbs reagent.

Original languageEnglish (US)
Pages (from-to)4238-4240
Number of pages3
JournalJournal of Organic Chemistry
Volume56
Issue number13
StatePublished - 1991

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Mevalonic Acid
Epoxidation
Epoxy Compounds
Hydrolysis
mevalonolactone
methylethyl ketone
lithium aluminum hydride
bis(trichlorohexylphosphine)benzylideneruthenium

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Bolitt, V., Mioskowski, C., Bhatt, R. K., & Falck, J. R. (1991). Synthesis of (S)-(+)-mevalonolactone and mevalonate analogues. Journal of Organic Chemistry, 56(13), 4238-4240.

Synthesis of (S)-(+)-mevalonolactone and mevalonate analogues. / Bolitt, Véronique; Mioskowski, Charles; Bhatt, R. K.; Falck, J R.

In: Journal of Organic Chemistry, Vol. 56, No. 13, 1991, p. 4238-4240.

Research output: Contribution to journalArticle

Bolitt, V, Mioskowski, C, Bhatt, RK & Falck, JR 1991, 'Synthesis of (S)-(+)-mevalonolactone and mevalonate analogues', Journal of Organic Chemistry, vol. 56, no. 13, pp. 4238-4240.
Bolitt, Véronique ; Mioskowski, Charles ; Bhatt, R. K. ; Falck, J R. / Synthesis of (S)-(+)-mevalonolactone and mevalonate analogues. In: Journal of Organic Chemistry. 1991 ; Vol. 56, No. 13. pp. 4238-4240.
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