Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 5, Pages 1346-1350Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201712065
Keywords
(3+2)-cycloaddition; aziridination; sulfur ylide; total synthesis; alpha-cyclopiazonic acid
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Funding
- EPSRC [EP/I038071/1]
- H2020 ERC [670668]
- University of Bristol
- EPSRC [EP/I038071/1, EP/K03927X/1, EP/L011999/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/L011999/1, EP/I038071/1, EP/K03927X/1] Funding Source: researchfish
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A convergent, nine-step (LLS), enantioselective synthesis of -cyclopiazonic acid and related natural products is reported. The route features a)an enantioselective aziridination of an imine with a chiral sulfur ylide; b)a bioinspired (3+2)-cycloaddition of the aziridine onto an alkene; and c)installation of the acetyltetramic acid by an unprecedented tandem carbonylative lactamization/N-O cleavage of a bromoisoxazole.
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