BIOMAT Database Logo BIOMAT Database Logo

Orthogonally Protected Diaminocyclopentenones as Synthons: Total Synthesis of (±)-Agelastatin A. 2023

Rafael F A Gomes, and João R Vale, and Juliana G Pereira, and Carlos A M Afonso
Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, Universidade de Lisboa, Avenida Professor Gama Pinto, 1649-003 Lisbon, Portugal.

Natural products containing aminocyclopentanes are common secondary metabolites, often biologically active. This work aims at the preparation of a useful synthon for total synthesis containing orthogonally protected amines. To this end, furfural and two amines were employed to form mixed trans-4,5-diaminocyclopentenones promoted by Cu(OTf)2. The selected amines can be orthogonally deprotected, allowing selective modification of the amines on the cyclopentane core. Their utility was showcased for the total synthesis of highly complex (±)-Agelastatin A.

UI MeSH Term Description Entries
D000470 Alkaloids Organic nitrogenous bases. Many alkaloids of medical importance occur in the animal and vegetable kingdoms, and some have been synthesized. (Grant & Hackh's Chemical Dictionary, 5th ed) Alkaloid,Plant Alkaloid,Plant Alkaloids,Alkaloid, Plant,Alkaloids, Plant
D000588 Amines A group of compounds derived from ammonia by substituting organic radicals for the hydrogens. (From Grant & Hackh's Chemical Dictionary, 5th ed) Amine
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D023303 Oxazolidinones Derivatives of oxazolidin-2-one. They represent an important class of synthetic antibiotic agents. 1,3-Oxazolidin-2-one,Oxazolidin-2-one,Oxazolidinone,1,3-Oxazolidine-2-one,2-Oxazolidone,2-oxazolidinone,1,3 Oxazolidin 2 one,1,3 Oxazolidine 2 one,2 Oxazolidone,2 oxazolidinone,Oxazolidin 2 one

Related Publications

Rafael F A Gomes, and João R Vale, and Juliana G Pereira, and Carlos A M Afonso
Total synthesis of (-)-agelastatin A.
December 2008, Organic letters,
Rafael F A Gomes, and João R Vale, and Juliana G Pereira, and Carlos A M Afonso
Synthesis of orthogonally protected lanthionines.
October 2003, The Journal of organic chemistry,
Rafael F A Gomes, and João R Vale, and Juliana G Pereira, and Carlos A M Afonso
Synthesis of Orthogonally Protected Labionin.
March 2021, The Journal of organic chemistry,
Rafael F A Gomes, and João R Vale, and Juliana G Pereira, and Carlos A M Afonso
Bioinspired total synthesis of agelastatin A.
July 2012, Angewandte Chemie (International ed. in English),
Rafael F A Gomes, and João R Vale, and Juliana G Pereira, and Carlos A M Afonso
Total synthesis of all (-)-Agelastatin alkaloids.
January 2010, Chemical science,
Rafael F A Gomes, and João R Vale, and Juliana G Pereira, and Carlos A M Afonso
Stereoselective synthesis of orthogonally protected alpha-methylnorlanthionine.
June 2006, Organic letters,
Rafael F A Gomes, and João R Vale, and Juliana G Pereira, and Carlos A M Afonso
Synthesis of orthogonally protected and functionalized bacillosamines.
April 2020, Organic & biomolecular chemistry,
Rafael F A Gomes, and João R Vale, and Juliana G Pereira, and Carlos A M Afonso
Synthesis of orthogonally protected disulfide bridge mimetics.
January 2011, The Journal of organic chemistry,
Rafael F A Gomes, and João R Vale, and Juliana G Pereira, and Carlos A M Afonso
Alkynyliodonium salts in organic synthesis. Application to the total synthesis of (-)-agelastatin A and (-)-agelastatin B.
August 2002, Journal of the American Chemical Society,
Rafael F A Gomes, and João R Vale, and Juliana G Pereira, and Carlos A M Afonso
Synthesis of orthogonally protected biaryl amino acid derivatives.
October 2006, Organic & biomolecular chemistry,
Copied contents to your clipboard!