Atom economic rhodium-catalyzed synthesis of lactones as key step for the construction of natural macrolactones

• Applicant: Professor Dr. Bernhard Breit
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: from 2016 to 2021
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 315326950

• Final Report Year: 2021

Final Report Abstract

Die Ziele des Projektes wurden vollumfänglich erreicht: Entwicklung einer enantioselektiven atomökonomischen Synthesemethode zum Aufbau von Makrolaktonen. - Entwicklung einer enantioselektiven atomökonomischen Synthesemethode zum Aufbau von Makrodioliden. - Erfolgreicher Einsatz der neuen Methoden in der Target-orientierten Synthese von Naturstoffen (Epothilon D, Vermiculin, Clavosolid A).

Publications

• “Atom-Economical Dimerization Strategy by the Rhodium-Catalyzed Addition of Carboxylic Acids to Allenes: Protecting-Group-Free Synthesis of Clavosolide A and Late-Stage Modification”. Angew. Chem. 2015, 127, 15750-15754; Angew. Chem. Int. Ed. 2015, 54,15530-15534
  A. M. Haydl, B. Breit
  (See online at https://doi.org/10.1002/ange.201506618 https://doi.org/10.1002/anie.201506618)
• “Enantioselective Rhodium-Catalyzed Atom-Economical Macrolactonization”. Angew. Chem. 2016, 128, 9890-9894; Angew. Chem. Int. Ed. 2016, 55, 9738-9742
  S. Ganss, B. Breit
  (See online at https://doi.org/10.1002/ange.201604301 https://doi.org/10.1002/anie.201604301)
• “The Total Synthesis of Epothilone D as a Yardstick for Probing New Methodologies”. Chem. Eur. J. 2017, 23, 541-545
  A. Haydl, B. Breit
  (See online at https://doi.org/10.1002/chem.201605011)
• “Enantioselective Rhodium-Catalyzed Dimerization of -Allenyl Carboxylic Acids: Straightforward Synthesis of C2-Symmetric Macrodiolides”. Angew. Chem. 2018, 130, 6682-6686; Angew. Chem. Int. Ed. 2018, 57, 6572-6576
  P. Steib, B. Breit
  (See online at https://doi.org/10.1002/anie.201803369)
• “Consice Total Synthesis of (-)-Vermiculine through a Rhodium-Catalyzed C2-symmetric Dimerization Strategy”. Chem. Eur. J. 2019, 25, 3532-3535
  P. Steib, B. Breit
  (See online at https://doi.org/10.1002/chem.201900216)