Total Synthesis of (-)-Antroalbocin A Enabled by a Strain Release-Controlled Photochemical 1,3-Acyl Shift - Research portal of Justus Liebig University Giessen:

Journal article

Total Synthesis of (-)-Antroalbocin A Enabled by a Strain Release-Controlled Photochemical 1,3-Acyl Shift

Authors list: Siekmeyer, B; Lübken, D; Bajerke, K; Bernhardt, B; Schreiner, PR; Kalesse, M

Publication year: 2022

Pages: 5812-5816

Journal: Organic Letters

Volume number: 24

Issue number: 31

ISSN: 1523-7060

eISSN: 1523-7052

Open access status: Green

DOI Link: https://doi.org/10.1021/acs.orglett.2c02347

Publisher: American Chemical Society

Abstract:
The first bioinspired, enantioselective, and protecting group free total synthesis of the antibacterial sesquiterpenoid (-)-antroalbocin A (1) has been achieved in 12 steps (5.4% overall yield) from dimedone. An organocatalytic Robinson annulation gave rapid access to the tricyclic enone (19) as starting material for the photochemical domino process of deconjugation and sigmatropic 1,3-acyl shift. Computational data of this process indicate that the 1,3-acyl shift benefits from the highly strained 1,3-enone 8. The transformation of 8 to its bridged isomer 5 is exergonic and, therefore, enables an increased conversion compared to unstrained substrates.

Authors/Editors

- Uni.-Prof. Dr. Peter Richard Schreiner, PhD

Citation Styles

Harvard Citation style: Siekmeyer, B., Lübken, D., Bajerke, K., Bernhardt, B., Schreiner, P. and Kalesse, M. (2022) Total Synthesis of (-)-Antroalbocin A Enabled by a Strain Release-Controlled Photochemical 1,3-Acyl Shift, Organic Letters, 24(31), pp. 5812-5816. https://doi.org/10.1021/acs.orglett.2c02347

APA Citation style: Siekmeyer, B., Lübken, D., Bajerke, K., Bernhardt, B., Schreiner, P., & Kalesse, M. (2022). Total Synthesis of (-)-Antroalbocin A Enabled by a Strain Release-Controlled Photochemical 1,3-Acyl Shift. Organic Letters. 24(31), 5812-5816. https://doi.org/10.1021/acs.orglett.2c02347