Asymmetric Total Synthesis of (-)-Dehydrocostus Lactone by Domino Metathesis

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An efficient total synthesis of the sesquiterpenoid (−)-dehydrocostus lactone is reported. Our earlier approach by a domino enediyne metathesis was extended by a domino dienyne metathesis strategy to give access to suitably functionalized hydroazulene cores. Highly stereoselective asymmetric anti aldol reactions provided the enantiopure substrates for this key step of our synthesis. Multiple hydroboration/oxidation of the resulting hydroazulenes set up three out of four stereogenic centers in a single step. First, oxidation to give a diketo-γ-lactone enabled an enantioselective formal synthesis of the target guaianolide. Subsequently, the final steps of this approach were improved by using a double carbonyl olefination at the stage of a masked γ-butyrolactone, which completed the synthesis in a much more efficient way.


Original languageEnglish
Pages (from-to)3535-3662
Number of pages8
JournalEuropean journal of organic chemistry: EurJOC
Issue number25
Publication statusPublished - 2021

External IDs

WOS 000674244100009
Scopus 85110532825