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

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

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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
Publication statusPublished - 1991

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ASJC Scopus subject areas

  • Organic Chemistry

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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.