Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 20, Issue 20, Pages 4135-4140Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2ob00692h
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Funding
- National Natural Science Foundation of China [U1801288, 82073695, 81903456]
- Frontiers Science Center for New Organic Matter [63181206]
- Natural Science Foundation of Tianjin [20JCQNJC02080, 20JCQNJC00960]
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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.
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.
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