Rapid Access to cis-1,3-Dialkylindanes: Asymmetric Formal Syntheses of epi-Mutisianthol and epi-Jungianol

Abstract

Concise and strategically unique asymmetric formal syntheses of epi-mutisianthol and epi-jungianol are presented. A novel disconnection approach is introduced to complement previous intramolecular cyclopentannulation strategies. Noteworthy features include: (a) control of the stereogenic benzylic carbon center through 1,3-chirality transfer from chiral indenols via the Johnson–Claisen rearrangement, which yields advanced indene-containing γ,δ-unsaturated esters, and (b) the diastereoselective construction of the cis-1,3-dialkylindane backbone via catalytic hydrogenation of the resulting indene. This approach presents a remarkable method for synthesizing structurally intriguing indane motifs.

Key words

epi-mutisianthol - epi-jungianol - cis-1,3-dialkylindane - Johnson–Claisen rearrangement - chirality transfer

Publikationsverlauf

Eingereicht: 15. Dezember 2023

Angenommen nach Revision: 18. Januar 2024

Accepted Manuscript online:
18. Januar 2024

Artikel online veröffentlicht:
12. Februar 2024

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