Sittihan S,
Jamison TF.
* Massachusetts Institute of Technology, Cambridge, USA
Total Synthesis of the Marine Ladder Polyether Gymnocin B.
J. Am. Chem. Soc. 2019;
141: 11239-11244
Key words
gymnocin B - marine ladder polyether - epoxide-opening cascade - modular synthesis
Significance
Sittihan and Jamison report the total synthesis of gymnocin B, the second largest
contiguous marine ladder polyether isolated to date. This complex target features
15 cyclic ether rings and 33 stereogenic centers, posing an exceptional synthetic
challenge. The authors succeeded in the preparation of gymnocin B by implementation
of bioinspired epoxide-opening cascades and a series of fragment couplings and cyclizations.
Comment
Key components D, E, and F were prepared from easily accessible compounds by exquisitely controlled epoxide-opening
cascades. Further elaboration of these building blocks allowed combination of subunits
G–J and construction of the remaining rings to afford the exceedingly challenging target
gymnocin B.
