|Total synthesis natural product sorangicin antibiotic macrolide carbo-Ferrier rearrangement|
The following thesis describes studies towards the total synthesis of sorangicins, the novel antibiotics from the gliding bacteria Sorangium cellulosum. Sorangicins can be retrosynthetically disconnected into four key fragments. The synthesis of two of these fragments is described. The dihydropyran fragment A can be synthesized by the carbo-Ferrier rearrangement of L-Glucal with allyltrimethylsilane. The following protecting group techniques, Swern oxidation, Grignard addition and oxidation with Dess-Martin periodinane yields the fully functionalized key fragment A. The side chain fragment B was synthesized using a 4R-Isopropyl-5.5-diphenyl-oxazolidin-2-on as a chiral auxiliary. The both fragments together with another two known are potential coupling partners for the total synthesis of sorangicins in the future projects.