Application of Lithiation-Borylation to the Total Synthesis of (-)-Rakicidin F

The stereochemistry of the lipophilic side chain of (+)-rakicidin F had not been determined until recently. Using our lithiation-borylation methodology (assembly line synthesis) we were able to efficiently prepare the all-syn isomer as well as the C-21 epimer of the side chain, and comparison with the natural product suggested that the natural product had all-syn stereochemistry. Completion of the total synthesis using a macrolactamization of the northern amide enabled us to confirm Wang and Chen's stereo chemical findings for the structure of (+)-rakicidin F.

Automated summary

The stereochemistry of the lipophilic side chain of (+)-rakicidin F has been determined recently through the efficient synthesis of all-syn isomers and comparison with the natural product. The completion of the total synthesis further confirmed the stereochemical findings of Wang and Chen for the structure of (+)-rakicidin F.