Total synthesis and structural confirmation of brevisamide, a new marine cyclic ether alkaloid from the dinoflagellate Karenia brevis.
The first total synthesis of brevisamide (1) has been accomplished in 21 linear steps starting from cis-but-2-ene-1,4-diol. A synthetic highlight is the Suzuki-Miyaura coupling between an ether ring fragment and a dienol side chain. This result confirmed the structure of 1 isolated from the dinoflagellate Karenia brevis.
Kuranaga
Takefumi
T
Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Shirai
Tomohiro
T
Baden
Daniel G
DG
Wright
Jeffrey L C
JL
Satake
Masayuki
M
Tachibana
Kazuo
K
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D000818:Animals; D004141:Dinoflagellida / Q000737:chemistry*; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis* / Q000737:chemistry*; D008968:Molecular Conformation; D011714:Pyrans; D013237:Stereoisomerism; D000095702:Polyether Toxins
D000470:Alkaloids; D005231:Fatty Acids, Unsaturated; D011714:Pyrans; C532303:brevisamide; D000095702:Polyether Toxins