Biomaterial Database

Synthesis of 7,6-Spirocyclic Imine with Butenolide Ring Provides Evidence for the Relative Configuration of Marine Toxin 13-desMe Spirolide C. 2019

Kou Minamino, and Michio Murata, and Hiroshi Tsuchikawa

Department of Chemistry, Faculty of Science , Osaka University , 1-1 Machikaneyama , Toyonaka , Osaka 560-0043 , Japan.

Efficient synthesis of the partial structure of marine toxin 13-desMe spirolide C was achieved via the selective Diels-Alder reaction and C-C bond formation with the use of a silatrane substituent and the subsequent facile formation of a γ-butenolide ring. The comparison of NMR data between the synthesized diastereomers and the natural product strongly suggested that the relative configuration at the C4 position was S configuration with respect to the 7,6-spirocycle.

UI	MeSH Term	Description	Entries
D007097	Imines	Organic compounds containing a carbon-nitrogen double bond where a NITROGEN atom can be attached to HYDROGEN or an alkyl or aryl group.	Imine
D008387	Marine Toxins	Toxic or poisonous substances elaborated by marine flora or fauna. They include also specific, characterized poisons or toxins for which there is no more specific heading, like those from poisonous FISHES.	Marine Biotoxins,Phycotoxins
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
D013237	Stereoisomerism	The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D015107	4-Butyrolactone	One of the FURANS with a carbonyl thereby forming a cyclic lactone. It is an endogenous compound made from gamma-aminobutyrate and is the precursor of gamma-hydroxybutyrate. It is also used as a pharmacological agent and solvent.	1,4-Butanolide,4-Hydroxybutyric Acid Lactone,Furanone, tetrahydro-2-,gamma-Butyrolactone,Dihydro-2(3H)-furanone,1,4 Butanolide,4 Butyrolactone,4 Hydroxybutyric Acid Lactone,Furanone, tetrahydro 2,Lactone, 4-Hydroxybutyric Acid,gamma Butyrolactone
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
D061565	Cycloaddition Reaction	Synthetic organic reactions that use reactions between unsaturated molecules to form cyclical products.	Cycloaddition,Cycloaddition Reaction Techniques,Diels-Alder Reaction,Cycloaddition Reaction Technique,Cycloaddition Reactions,Diels Alder Reaction,Reaction Technique, Cycloaddition,Reaction Techniques, Cycloaddition,Reaction, Cycloaddition,Reaction, Diels-Alder,Reactions, Cycloaddition,Technique, Cycloaddition Reaction,Techniques, Cycloaddition Reaction