BIOMAT Database Logo BIOMAT Database Logo

Total synthesis of the putative structure of stemonidine: the definitive proof of misassignment. 2007

Francisco Sánchez-Izquierdo, and Pilar Blanco, and Félix Busqué, and Ramón Alibés, and Pedro de March, and Marta Figueredo, and Josep Font, and Teodor Parella
Universitat Autonoma de Barcelona, Departament de Química, 08193 Bellaterra, Spain.

[structure: see text] The total synthesis of the putative structure of the Stemona alkaloid stemonidine has been completed. The key transformations include a 1,3-dipolar cycloaddition of a chiral nitrone derived from (S)-prolinol and a spirolactonization process involving the generation of the critical stereocenter. The NMR data of the synthetic material do not match those reported for the natural product. It is concluded that the structure assigned to stemonidine is incorrect, and it must be reassigned as stemospironine.

UI MeSH Term Description Entries
D007783 Lactones Cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure. Large cyclic lactones of over a dozen atoms are MACROLIDES. Lactone
D009589 Nitrogen Oxides Inorganic oxides that contain nitrogen. Nitrogen Oxide,Oxide, Nitrogen,Oxides, Nitrogen
D009682 Magnetic Resonance Spectroscopy Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING). In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
D009930 Organic Chemicals A broad class of substances containing carbon and its derivatives. Many of these chemicals will frequently contain hydrogen with or without oxygen, nitrogen, sulfur, phosphorus, and other elements. They exist in either carbon chain or carbon ring form. Organic Chemical,Chemical, Organic,Chemicals, Organic
D011759 Pyrrolidines Compounds also known as tetrahydropyridines with general molecular formula (CH2)4NH. Tetrahydropyridine,Tetrahydropyridines
D006573 Heterocyclic Compounds, 1-Ring Organic compounds that contain a ring structure made up of carbon and one or more additional elements such as nitrogen and oxygen. Heterocyclic Cpds, 1-Ring,1-Ring Heterocyclic Compounds,1-Ring Heterocyclic Cpds,Heterocyclic Compounds, 1 Ring,Heterocyclic Cpds, 1 Ring
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
D001372 Aza Compounds Organic chemicals where carbon atoms have been replaced by nitrogen atoms. Compounds, Aza
D013141 Spiro Compounds Cyclic compounds that include two rings which share a single atom (usually a carbon). The simplest example of this type of compound is Spiro[2.2]pentane, which looks like a bow tie. Compounds, Spiro
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

Related Publications

Francisco Sánchez-Izquierdo, and Pilar Blanco, and Félix Busqué, and Ramón Alibés, and Pedro de March, and Marta Figueredo, and Josep Font, and Teodor Parella
Total synthesis of the putative structure of xylarinol B.
June 2014, Chemistry, an Asian journal,
Francisco Sánchez-Izquierdo, and Pilar Blanco, and Félix Busqué, and Ramón Alibés, and Pedro de March, and Marta Figueredo, and Josep Font, and Teodor Parella
Total synthesis of the putative structure of nagelamide D.
April 2009, Organic letters,
Francisco Sánchez-Izquierdo, and Pilar Blanco, and Félix Busqué, and Ramón Alibés, and Pedro de March, and Marta Figueredo, and Josep Font, and Teodor Parella
Total synthesis of the putative structure of lucentamycin A.
November 2009, Organic letters,
Francisco Sánchez-Izquierdo, and Pilar Blanco, and Félix Busqué, and Ramón Alibés, and Pedro de March, and Marta Figueredo, and Josep Font, and Teodor Parella
Stereoselective total synthesis of the putative structure of nitraraine.
August 2014, The Journal of organic chemistry,
Francisco Sánchez-Izquierdo, and Pilar Blanco, and Félix Busqué, and Ramón Alibés, and Pedro de March, and Marta Figueredo, and Josep Font, and Teodor Parella
Asymmetric Total Synthesis of the Putative Structure of Diplopyrone.
May 2017, The Journal of organic chemistry,
Francisco Sánchez-Izquierdo, and Pilar Blanco, and Félix Busqué, and Ramón Alibés, and Pedro de March, and Marta Figueredo, and Josep Font, and Teodor Parella
Total synthesis and proof of structure of mycothiol bimane.
April 2002, Journal of the American Chemical Society,
Francisco Sánchez-Izquierdo, and Pilar Blanco, and Félix Busqué, and Ramón Alibés, and Pedro de March, and Marta Figueredo, and Josep Font, and Teodor Parella
Total synthesis of the putative structure of the proposed Banyasin A.
January 2015, Frontiers in chemistry,
Francisco Sánchez-Izquierdo, and Pilar Blanco, and Félix Busqué, and Ramón Alibés, and Pedro de March, and Marta Figueredo, and Josep Font, and Teodor Parella
Total synthesis of the putative structure of the lupin alkaloid plumerinine.
May 2002, Organic letters,
Francisco Sánchez-Izquierdo, and Pilar Blanco, and Félix Busqué, and Ramón Alibés, and Pedro de March, and Marta Figueredo, and Josep Font, and Teodor Parella
Solid-phase total synthesis and structure proof of callipeltin B.
December 2006, Journal of the American Chemical Society,
Francisco Sánchez-Izquierdo, and Pilar Blanco, and Félix Busqué, and Ramón Alibés, and Pedro de March, and Marta Figueredo, and Josep Font, and Teodor Parella
FR901464: total synthesis, proof of structure, and evaluation of synthetic analogues.
October 2001, Journal of the American Chemical Society,
Copied contents to your clipboard!