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

Publikation: Beitrag in FachzeitschriftForschungsartikelBeigetragenBegutachtung

Beitragende

Abstract

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.

Details

OriginalspracheEnglisch
Seiten (von - bis)3579-3586
Seitenumfang8
FachzeitschriftEuropean journal of organic chemistry: EurJOC
Jahrgang2021
Ausgabenummer25
PublikationsstatusVeröffentlicht - Juli 2021
Peer-Review-StatusJa

Externe IDs

WOS 000674244100009
Scopus 85110532825
Mendeley 2e25685f-f6b8-3567-bf4c-cf3fe073b5d7

Schlagworte