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DOI: 10.1055/a-2249-2326
Rapid Access to cis-1,3-Dialkylindanes: Asymmetric Formal Syntheses of epi-Mutisianthol and epi-Jungianol
This work was supported by a 2-Year Research Grant of Pusan National University.
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 transferSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2249-2326.
- Supporting Information
Publication History
Received: 15 December 2023
Accepted after revision: 18 January 2024
Accepted Manuscript online:
18 January 2024
Article published online:
12 February 2024
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