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Beilstein J. Org. Chem. 2015, 11, 1514–1519, doi:10.3762/bjoc.11.165
Graphical Abstract
Figure 1: Retrosynthetic approach to hybrid cyclophane derivative 1.
Scheme 1: Attempted synthesis of thiophenophane derivative 2.
Scheme 2: Synthesis of hybrid cyclophane 1.
Figure 2: The molecular crystal structure of 1 with 50% probability [41].
Scheme 3: Attempted synthesis of thiophenophane derivative 2a.
Scheme 4: Synthesis of cyclophane 1a with a thiophene and an indole moiety.
Beilstein J. Org. Chem. 2015, 11, 1123–1128, doi:10.3762/bjoc.11.126
Figure 1: Natural and non-natural products containing quinane systems.
Figure 2: Quinane building blocks (1–3) and metathetic catalyst used in our strategy.
Scheme 1: Synthesis of tricyclic diones 5 and 2.
Figure 3: Retrosynthetic approach to aza-polyquinane 6 and spiro-polyquinane 7.
Scheme 2: Synthesis of the diindole derivative 9 Reagents and conditions: (i) TA:DMU, PhNHNH3Cl, 70 °C, 6 h, ...
Scheme 3: Synthesis of the macrocyclic aza-polyquinane derivative 6. Reagents and conditions: (i) NaH, allyl ...
Scheme 4: Synthesis of the spiro-polyquinane 7. Reagents and conditions: (i) NaH, allyl bromide, THF, rt, 24 ...
Scheme 5: General strategy to bis-spirocycles via RCM.
Beilstein J. Org. Chem. 2013, 9, 2709–2714, doi:10.3762/bjoc.9.307
Figure 1: [4.4.2] and [1.1.1]propellanes.
Figure 2: Alkaloids containing indole-based propellanes.
Figure 3: Retrosynthetic strategy to indole-based propellane 4.
Scheme 1: Preparation of diindole dione 2.
Scheme 2: Synthesis of allylated indole derivatives 3, 7 and 8.
Scheme 3: Synthesis of indole-based propellane derivatives 4 and 11 by RCM route.
Scheme 4: Synthesis of 4 by Weiss–Cook condensation and two fold Fischer indole cyclization.