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Beilstein J. Org. Chem. 2016, 12, 985–999, doi:10.3762/bjoc.12.97
Graphical Abstract
Figure 1: Bridged polycyclic natural products.
Figure 2: Strategic limitations.
Scheme 1: Bridged rings from N–H bond insertions.
Scheme 2: The synthesis of deoxystemodin.
Scheme 3: A model system for ingenol.
Scheme 4: Formal synthesis of platensimycin.
Scheme 5: The formal synthesis of gerryine.
Scheme 6: Copper-catalyzed bridged-ring synthesis.
Scheme 7: Factors influencing insertion selectivity.
Scheme 8: Bridged-lactam formation.
Scheme 9: The total synthesis of (+)-codeine.
Scheme 10: A model system for irroratin.
Scheme 11: The utility of 1,6-insertion.
Scheme 12: Piperidine functionalization.
Scheme 13: Wilkinson’s catalyst for C–H bond insertion.
Scheme 14: Bridgehead insertion and the total synthesis of albene and santalene.
Scheme 15: The total synthesis of neopupukean-10-one.
Scheme 16: An approach to phomoidride B.
Scheme 17: Carbene cascade for fused bicycles.
Scheme 18: Cascade formation of bridged rings.
Scheme 19: Conformational effects.
Scheme 20: Hydrazone cascade reaction.
Scheme 21: Mechanistic studies.
Scheme 22: Gold carbene formation from alkynes.
Scheme 23: Au-catalyzed bridged-bicycle formation.
Scheme 24: Gold carbene/alkyne cascade.
Scheme 25: Gold carbene/alkyne cascade with C–H bond insertion.
Scheme 26: Platinum cascades.
Scheme 27: Tungsten cascade.