Convergent strategies for the total synthesis of polycyclic ether marine metabolites.
Marine polycyclic ether natural products continue to fascinate chemists and biologists due to their exceptionally large and complex molecular architectures and potent and diverse biological activities. Tremendous progress has been made over the past decade toward the total synthesis of marine polycyclic ether natural products. In this area, a convergent strategy for assembling small fragments into an entire molecule always plays a key role in successful total synthesis. This review describes our efforts to develop convergent strategies for the synthesis of polycyclic ethers and their application to the total synthesis of gambierol, gymnocin-A, and brevenal, and to the partial synthesis of the central part of ciguatoxins and the nonacyclic polyether skeleton of gambieric acids.
Sasaki
Makoto
M
Laboratory of Biostructural Chemistry, Graduate School of Life Sciences, Tohoku University, 1-1 Tsutsumidori-amamiya, Aoba-ku, Sendai 981-8555, Japan. masasaki@bios.tohoku.ac.jp
Fuwa
Haruhiko
H
D002922:Ciguatoxins / Q000138:chemical synthesis / Q000737:chemistry; D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D008386:Marine Biology; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013874:Thiopental / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D035964:Oxocins
D002922:Ciguatoxins; D004988:Ethers, Cyclic; D011083:Polycyclic Compounds; D013874:Thiopental; C435770:gambierol; D035964:Oxocins; C458159:gymnocin A; C004316:thiobutabarbital