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

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 ca...

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Veröffentlicht in:Synthesis (Stuttgart) 2024-12, Vol.56 (9), p.1401-1406
Hauptverfasser: Tran, Cong So, Yoon, Moonsang, Le, Long Duc, Kim, Seoyeong, Kim, Huiae, Kim, Jisu, Nguyen, Long Huu, Koh, Minseob, Yun, Hwayoung
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:0039-7881
1437-210X
DOI:10.1055/a-2249-2326