American Chemical Society
ol8b01629_si_002.pdf (7.34 MB)

Progress toward the Total Synthesis of Gukulenin A: Photochemically Triggered Two-Carbon Ring Expansion Key to α‑Tropolonic Ether Synthesis

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journal contribution
posted on 2018-06-19, 18:36 authored by David Tymann, Ulf Bednarzick, Ljuba Iovkova-Berends, Martin Hiersemann
The ex-chiral-pool synthesis of an advanced gukulenin A precursor from (−)-piperitone is revealed. Key C/C connecting maneuvers to the synthesis of a C2 dissymmetric bis­(α-tropolonic) ether building block are a ring-contracting Meinwald rearrangement, a photochemically triggered two-carbon ring expansion, and a homodimerization by cross-metathesis.