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Beilstein J. Org. Chem. 2018, 14, 2597–2601, doi:10.3762/bjoc.14.237
Graphical Abstract
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.