We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Copper-Catalyzed Double Additions and Radical Cyclization Cascades in the Re-Engineering of the Antibacterial Pleuromutilin.
- Authors
Ruscoe, Rebecca E.; Fazakerley, Neal J.; Huang, Huanming; Flitsch, Sabine; Procter, David J.
- Abstract
A general synthetic sequence involving simply prepared starting materials provides rapid access to diverse, novel tricyclic architectures inspired by pleuromutilin. SmII-mediated radical cyclization cascades of dialdehydes, prepared using a new, one-pot, copper-catalyzed double organomagnesium addition to β-chlorocyclohexenone, proceed with complete sequence selectivity and typically with high diastereocontrol to give analogues of the target core. Our expedient approach (ca. 7 steps) allows non-traditional, de novo synthetic access to analogues of the important antibacterial that can't be prepared from the natural product by semisynthesis.
- Subjects
RING formation (Chemistry); ORGANOMAGNESIUM compounds; ELECTRON-transfer catalysis; ALDEHYDE synthesis; DIASTEREOISOMERS synthesis
- Publication
Chemistry - A European Journal, 2016, Vol 22, Issue 1, p116
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201504343