NEW POLYCHLORINATED AMINO-ACID DERIVATIVES FROM THE MARINE SPONGE DYSIDEA-HERBACEA

Citation
Md. Unson et al., NEW POLYCHLORINATED AMINO-ACID DERIVATIVES FROM THE MARINE SPONGE DYSIDEA-HERBACEA, Journal of organic chemistry, 58(23), 1993, pp. 6336-6343
Citations number
26
Categorie Soggetti
Chemistry Inorganic & Nuclear
ISSN journal
00223263
Volume
58
Issue
23
Year of publication
1993
Pages
6336 - 6343
Database
ISI
SICI code
0022-3263(1993)58:23<6336:NPADFT>2.0.ZU;2-S
Abstract
A new series of polychlorinated amino acid derivatives were isolated f rom the tropical marine sponge Dysidea herbacea (Dictyoceratida). Two major hexachlorinated metabolites, dysideathiazole (4) and N-methyldys ideathiazole (5), and a minor pentachlorinated compound, 10-dechloro-N -methyldysideathiazole (6), were isolated from a specimen from Pohnpei . 10-Dechlorodysideathiazole (7) was isolated as a minor constituent o f a Palauan specimen, together with the major metabolites 9,10-didechl oro-N-methyldysideathiazole (8) and 10-dechloro-N-methyldysideathiazol e (6). A second specimen from Palau contained dysideapyrrolidone (9). The structures of 4-9 were elucidated by spectroscopic methods. The ab solute stereochemistry of compounds 4-6 was determined by X-ray crysta llography of the natural products and of the carbamate derivative 17 t o be S at all chiral centers.