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Beilstein J. Org. Chem. 2020, 16, 1111–1123, doi:10.3762/bjoc.16.98
Graphical Abstract
Figure 1: (a) General scheme for truxillic acid derivatives; (b) general scheme for symmetric 1,3-diaminotrux...
Figure 2: (a) (Z)-4-Arylidene-2-aryl-5(4H)-oxazolones used for the synthesis of 1,3-diaminotruxillic derivati...
Figure 3: (Z)-4-Arylidene-2((E)-styryl)-5(4H)-oxazolones 2a–j used in this work and overall reaction scheme.
Figure 4: Molecular drawing of the oxazolone 2c.
Scheme 1: Ortho-palladation of oxazolones 2 by treatment with Pd(OAc)2 and different structures obtained for ...
Scheme 2: [2 + 2] Photocycloaddition of cyclopalladated complexes 3 in solution to give the dinuclear cyclobu...
Figure 5: Molecular drawing of cyclobutane ortho-palladated 4a. Ellipsoids are shown at the 50% probability l...
Scheme 3: Release of the 1,3-diaminotruxillic bis-amino ester derivatives 5 by methoxycarbonylation of the Pd...
Beilstein J. Org. Chem. 2018, 14, 2597–2601, doi:10.3762/bjoc.14.237
Figure 1: Previous synthetic approaches to 3a-substituted cis-hydrindan-2,4-diones.
Scheme 1: Decahydroquinoline 1 as a versatile building block for Lycopodium alkaloid synthesis.
Figure 2: Examples of Lycopodium alkaloids synthesized from 3a-substituted hydrindan-2,4-diones.
Scheme 2: A de novo approach to 3a-substituted cis-hydrindan-2,4-diones.
Scheme 3: Synthesis of enone 4 and the Danheiser annulation. The depicted compounds are all racemic.
Scheme 4: Transformation of the vinylsilane moiety to ketone 8.
Figure 3: Stereoview of cis-hydrindane 8.