AI Article Synopsis
- An innovative method for rearranging β-lactams has been introduced, allowing for the creation of various γ-butyrolactams.
- This reaction is unique because it likely operates through a dual-activation process, leading to distinct reactivity and selectivity compared to traditional β-lactone rearrangements.
- Studies show that the mechanism of this rearrangement can vary based on the type of groups involved (hydrogen, alkyl, or aryl), and this approach has successfully enabled the synthesis of complex marine alkaloids in relatively few steps.
Article Abstract
An unprecedented dyotropic rearrangement of β-lactams has been developed, which provides an enabling tool for the synthesis of structurally diverse γ-butyrolactams. Unlike the well-established dyotropic rearrangements of β-lactones, the present reaction probably proceeds through a dual-activation mode, and thus displays unusual reactivity and chemoselectivity. The combined computational and experimental results suggest that the dyotropic rearrangement of β-lactams may proceed through different mechanisms depending on the nature of migrating groups (H, alkyl, or aryl). Hinging on a chemoselective H-migration dyotropic rearrangement of β-lactams, we have completed the divergent synthesis of tricyclic marine alkaloids (-)-lepadiformine A, (+)-cylindricine C, and (-)-fasicularin within 11-12 longest linear steps.
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| http://dx.doi.org/10.1002/anie.202414985 | DOI Listing |
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