50906-95-1Relevant academic research and scientific papers
Asymmetric Synthesis of (+)-Nemorensic Acid - Revision of the Stereochemistry of the Pyrrolizidine Alkaloid Nemorensine
Dillon, Michael P.,Lee, Nadine C.,Stappenbeck, Frank,White, James D.
, p. 1645 - 1646 (1995)
(+)-Nemorensic acid, the necic acid constituent of the pyrrolizidine alkaloid nemorensine, is shown to be (2R,3R,5S)-2-carboxy-2,3,5-trimethyltetrahydrofuranacetic acid by synthesis from (R)-(+)-β-citronellol, and a corrected structure for the parent alkaloid nemorensine is established by a single crystal X-ray analysis.
Enantiospecific Synthesis of (+)-Nemorensic Acid, a Necic Acid Component of the Macropyrrolizidine Alkaloid, Nemorensine
Honda, Toshio,Ishikawa, Fumihiro
, p. 5542 - 5546 (2007/10/03)
A concise enantiospecific synthesis of nemorensic acid 3, a necic acid component of the macropyrrolizidine alkaloid nemorensine 2, isolated from Senecio nemorensis L., is described. Reaction of an ∈-halo-α,β-unsaturated ester (8), readily accessible from a monoterpene (-)-carvone, with samarium iodide gave a fragmentation product (9), where a carbon-carbon bond cleavage reaction occurred between the γ and δ positions of the carbonyl group, regioselectively. Deprotection of the silyl group of 9 brought about an intramolecular cyclization to provide tetrahydrofuran derivatives (10), which, upon chemical modification of the side chain, gave nemorensic acid.
OXYNEMORENSINE, AN ALKALOID FROM Senecio nemorensis L., VAR. subdecurrens GRISEB.
Klasek, Antonin,Sedmera, Petr,Vokoun, Jindrich,Boeva, Anna,Dvorackova, Svatava,Santavy, Frantisek
, p. 548 - 558 (2007/10/02)
From S. nemorensis L., var. subdecurrens GRISEB. there were isolated the previously obtained alkaloids nemorensine (I), retroisosenine (II), bulgarsenine (III) and, in addition, the alkaloid oxynemorensine which was assigned the structure VIII on the basis of the interpretation of the 1H-NMR, 13C-NMR, mass spectra, and on that of the identification of the products of hydrolysis and reduction.Furthemore, the isolation of the cis-nemorensic acid (V) as well as that of the unsaturated acid IV, and the transformation of bulgarsenine (III) to nemorensine (I) were described.
