Total synthesis of the proposed structure of brevenal.
Total synthesis of the proposed structure of brevenal, a natural marine polycyclic ether product, has been accomplished. The synthesis features (i) convergent synthesis of the pentacyclic polyether skeleton using our developed Suzuki-Miyaura coupling strategy and (ii) construction of the multi-substituted dienal side chain by CuTC-mediated Stille reaction. Comparison of the NMR data of the synthetic compound with those reported for the natural product revealed that the proposed structure of brevenal needs to be revised.
Fuwa
Haruhiko
H
Laboratory of Biostructural Chemistry, Graduate School of Life Sciences, Tohoku University, Tsutsumidori-amamiya, Aoba-ku, Sendai 981-8555, Japan.
Ebine
Makoto
M
Sasaki
Makoto
M
D015394:Molecular Structure; D013874:Thiopental / Q000031:analogs & derivatives* / Q000138:chemical synthesis
C004316:thiobutabarbital; D013874:Thiopental