Total synthesis of brevisamide.
The second total synthesis of Brevisamide, a marine cyclic ether alkaloid from Karenia brevis, is reported. This streamlined synthesis proceeds in 21 steps, 14 steps longest linear sequence, in 5.2% overall yield and features a key SmI(2) reductive cyclization step to access the tetrasubstituted pyran core.
Fadeyi
Olugbeminiyi O
OO
Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37232, USA.
Lindsley
Craig W
CW
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D003500:Cyclization; D004141:Dinoflagellida / Q000737:chemistry; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis; D000095702:Polyether Toxins
D000470:Alkaloids; D005231:Fatty Acids, Unsaturated; D011714:Pyrans; C532303:brevisamide; D000095702:Polyether Toxins