Intramolecular Cyclization During Bromination of the Quinoline Alkaloid Haplophyllidine.

Bromination of the furanoquinoline alkaloid haplophyllidine by molecular bromine and N-bromosuccinimide was accompanied by intramolecular cyclization to form mixtures of new compounds containing additional penta-, hexa-, and spirocyclic rings incorporating the prenyl group of haplophyllidine. The structures and absolute configurations of the chiral centers of all four bromo-derivatives were elucidated using a combination of NMR spectroscopic methods and X-ray crystal structure analyses.

Rinderidine and oblongifolidine new pyrrolizidine alkaloids from Rindera oblongifolia M. Popov and their absolute configurations.

The alkaloid composition of Rindera oblongifolia was studied, in which the pyrrolizidine alkaloids echinatine and trachelanthamine N-oxide, as well as two new quaternary salts namely rinderidine and the oblongifolidine were isolated. The structures of the isolated new alkaloids were elucidated by NMR spectroscopy. The absolute configuration of lindelofine, trachelanthamine N-oxide, rinderidine and oblongifolidine was established by single crystal X-ray diffraction as: 1 R, 4 R, 8 R, 2'S, 3'R; 1 R, 4S, 8S, 2'S, 3'R; 4 R, 7S, 8 R, 2'S, 3'S; 4 R, 7S, 8 R, 2'S, 3'S (7''S, 8''R) respectively. Both new pyrrolizidine alkaloids showed no cytotoxicity against four cancer cell lines such as HeLa, НEр-2, HBL-100 and CCRF-CEM.