Total synthesis of gambierol.
[structure: see text] The first total synthesis of gambierol, a marine polycyclic ether toxin, has been achieved. The synthesis features the Pd(PPh3)4/CuCl/LiCl-promoted Stille coupling for the stereoselective construction of the sensitive triene side chain that includes a conjugated (Z,Z)-diene moiety.
Fuwa
Haruhiko
H
Department of Chemistry, Graduate School of Science, The University of Tokyo, Tokyo 113-0033, Japan.
Sasaki
Makoto
M
Satake
Masayuki
M
Tachibana
Kazuo
K
D000818:Animals; D002922:Ciguatoxins; D004141:Dinoflagellida / Q000737:chemistry; D004988:Ethers, Cyclic / Q000138:chemical synthesis*; D008387:Marine Toxins / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D011083:Polycyclic Compounds / Q000138:chemical synthesis*; D011090:Polyenes / Q000737:chemistry; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry; D035964:Oxocins
D002922:Ciguatoxins; D004988:Ethers, Cyclic; D008387:Marine Toxins; D010165:Palladium; D011083:Polycyclic Compounds; D011090:Polyenes; D014753:Vinyl Compounds; C435770:gambierol; D035964:Oxocins; C003763:vinyl bromide