Syntheses of polybrominated indoles from the red alga Laurencia brongniartii and the brittle star Ophiocoma erinaceus.
The red alga Laurencia brongniartii and brittle star Ophiocoma erinaceus metabolites 2,3,6-tribromo-1-methylindole (1) and 2,3,5,6-tetrabromo-1-methylindole (2) are easily synthesized selectively from 2,3-dibromo-1-methylindole (5), which in turn is prepared from indole (3) in one continuous sequence in 92% yield. Moreover, 2 can be made from both 1 and 5 in 67% and 65% yields, respectively.
Liu
Yanbing
Y
Department of Chemistry, Dartmouth College, Hanover, New Hampshire 03755-3564, USA.
Gribble
Gordon W
GW
D000818:Animals; D002384:Catalysis; D004447:Echinodermata / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D000461:Rhodophyta / Q000737:chemistry*
C460133:2,3,5,6-tetrabromo-1-methylindole; C460132:2,3,6-tribromo-1-methylindole; C460131:2,3-dibromo-1-methylindole; D007211:Indoles