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Beilstein J. Org. Chem. 2013, 9, 1179–1184, doi:10.3762/bjoc.9.132
Graphical Abstract
Figure 1: Lyconadin A.
Scheme 1: Retrosynthetic analysis of 1.
Scheme 2: Synthesis of triether 15.
Scheme 3: Synthesis and attempted ring-opening of epoxide 17.
Scheme 4: Attempted protection of 14 and silyl migration.
Scheme 5: Synthesis and ring-opening rearrangement of epoxide 25.
Scheme 6: Proposed mechanism for generation of alcohol 26.
Scheme 7: Synthesis of epoxide 29 from alcohol 26 (asterisks indicate relative but not absolute stereochemist...