Enantioselective Synthesis of the Platensimycin Core by Silver(I)-Promoted Cyclization of Δ 6 -α-Iodoketone
Abstract
A chiral-pool-based synthesis of the platensimycin core was achieved using (S)-lactic acid as an inexpensive starting material. The cyclohexenone ring was closed in a Mukaiyama–Michael domino sequence, while the quaternary stereocenter was created by a highly stereoselective decarboxylative allylation. The spirobicyclic skeleton was constructed by a RCM reaction. A new silver(I)-promoted cyclization reaction of Δ 6 - and Δ 7 -α-iodoketones was developed and applied for the pivotal carbon–carbon bond formation. The scope and limitations of this methodology are also presented.
Keywords:
antibiotics / cyclization / natural products / silver / total synthesisSource:
Chemistry - A European Journal, 2019, 25, 17, 4340-4344Publisher:
- Wiley
Funding / projects:
- The development of new synthetic methods and their application in the synthesis of natural products and biologically active molecules (RS-172027)
- Reinforcement of the Faculty of Chemistry, University of Belgrade, towards becoming a Center of Excellence in the region of WB for Molecular Biotechnology and Food research (EU-256716)
Note:
- This is the peer-reviewed version of the following article:Trajković, M.; Ferjančić, Z.; Saičić, R. N.; Bihelović, F. Enantioselective Synthesis of the Platensimycin Core by Silver(I)-Promoted Cyclization of Δ 6 -α-Iodoketone. Chemistry - A European Journal 2019, 25 (17), 4340–4344. https://doi.org/10.1002/chem.201900497.
- Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3842
DOI: 10.1002/chem.201900497
ISSN: 0947-6539