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Enantioselective Synthesis of the Platensimycin Core by Silver(I)-Promoted Cyclization of Δ 6 -α-Iodoketone

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2019
10.1002@chem.201900497.pdf (949.5Kb)
Authors
Trajković, Milos
Ferjančić, Zorana
Saičić, Radomir
Bihelović, Filip
Article (Accepted Version)
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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 synthesis
Source:
Chemistry - A European Journal, 2019, 25, 17, 4340-4344
Publisher:
  • 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

WoS: 000462057300014

Scopus: 2-s2.0-85062044339
[ Google Scholar ]
1
1
URI
https://cherry.chem.bg.ac.rs/handle/123456789/2874
Collections
  • Publikacije
Institution/Community
Hemijski fakultet
TY  - JOUR
AU  - Trajković, Milos
AU  - Ferjančić, Zorana
AU  - Saičić, Radomir
AU  - Bihelović, Filip
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2874
AB  - 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.
PB  - Wiley
T2  - Chemistry - A European Journal
T1  - Enantioselective Synthesis of the Platensimycin Core by Silver(I)-Promoted Cyclization of Δ 6 -α-Iodoketone
VL  - 25
IS  - 17
SP  - 4340
EP  - 4344
DO  - 10.1002/chem.201900497
ER  - 
@article{
author = "Trajković, Milos and Ferjančić, Zorana and Saičić, Radomir and Bihelović, Filip",
year = "2019",
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.",
publisher = "Wiley",
journal = "Chemistry - A European Journal",
title = "Enantioselective Synthesis of the Platensimycin Core by Silver(I)-Promoted Cyclization of Δ 6 -α-Iodoketone",
volume = "25",
number = "17",
pages = "4340-4344",
doi = "10.1002/chem.201900497"
}
Trajković, M., Ferjančić, Z., Saičić, R.,& Bihelović, F.. (2019). Enantioselective Synthesis of the Platensimycin Core by Silver(I)-Promoted Cyclization of Δ 6 -α-Iodoketone. in Chemistry - A European Journal
Wiley., 25(17), 4340-4344.
https://doi.org/10.1002/chem.201900497
Trajković M, Ferjančić Z, Saičić R, Bihelović F. Enantioselective Synthesis of the Platensimycin Core by Silver(I)-Promoted Cyclization of Δ 6 -α-Iodoketone. in Chemistry - A European Journal. 2019;25(17):4340-4344.
doi:10.1002/chem.201900497 .
Trajković, Milos, Ferjančić, Zorana, Saičić, Radomir, Bihelović, Filip, "Enantioselective Synthesis of the Platensimycin Core by Silver(I)-Promoted Cyclization of Δ 6 -α-Iodoketone" in Chemistry - A European Journal, 25, no. 17 (2019):4340-4344,
https://doi.org/10.1002/chem.201900497 . .

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