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Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides.
Zhurakovskyi, Oleksandr; Türkmen, Yunus E; Löffler, Lorenz E; Moorthie, Vijayalakshmi A; Chen, C Chun; Shaw, Michael A; Crimmin, Mark R; Ferrara, Marco; Ahmad, Mushtaq; Ostovar, Mehrnoosh; Matlock, Johnathan V; Aggarwal, Varinder K.
Affiliation
  • Zhurakovskyi O; School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
  • Türkmen YE; School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
  • Löffler LE; School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
  • Moorthie VA; School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
  • Chen CC; School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
  • Shaw MA; School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
  • Crimmin MR; School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
  • Ferrara M; School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
  • Ahmad M; School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
  • Ostovar M; School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
  • Matlock JV; School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
  • Aggarwal VK; School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
Angew Chem Int Ed Engl ; 57(5): 1346-1350, 2018 01 26.
Article in En | MEDLINE | ID: mdl-29265694
ABSTRACT
A convergent, nine-step (LLS), enantioselective synthesis of α-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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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Angew Chem Int Ed Engl Year: 2018 Type: Article Affiliation country: United kingdom
Fulltext
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Angew Chem Int Ed Engl Year: 2018 Type: Article Affiliation country: United kingdom