Total synthesis and stereochemical assignment of rakicidin F

Total synthesis of rakicidin F was accomplished in 20 linear steps (0.68% overall yield), which enabled the configural determination of its six stereogenic centers as 2R, 15R, 16R, 17S, 19S, and 21S. The macrolactonization of the rakicidin linear precursor was investigated and the unsuccessful results might be attributed to the steric hindrance near C16-OH.

Automated summary

In this study, the total synthesis of rakicidin F was successfully achieved, allowing the determination of its stereogenic centers. The macrolactonization reaction of rakicidin precursor was also investigated, with steric hindrance near C16-OH identified as a possible cause for the unsuccessful results.