The synthesis of polyfunctionalized, cyclohexene-based chirons from tartaric acid

Joshua N. Buckler, Brett D. Schwartz, Martin G. Banwell*

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    7 Citations (Scopus)

    Abstract

    Compound ent-1 as well as certain related homochiral and polyfunctionalized cyclohexenes have been prepared from the 1,2-diacetal 4 that is itself readily derived from L-tartaric acid (3). Grignard addition and ring-closing metathesis processes constitute the key steps associated with the reaction sequences involved. This work provides a method for obtaining a range of potentially useful cyclohexenone-containing chirons that are enantiomerically related to those that have been prepared from the homochiral cis-1,2-dihydrocatechol 2, the product of the microbial biotransformation of bromobenzene.

    Original languageEnglish
    Pages (from-to)290-303
    Number of pages14
    JournalHeterocycles
    Volume95
    Issue number1
    DOIs
    Publication statusPublished - 2017

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