Studies on the synthesis of the "northern" and "southern" segments of boromycin and aplasmomycin Public Deposited

http://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/4x51hn59v

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  • The stereocontrolled synthesis of the southern lactone 17 of boromycin and of the northern segments of both boromycin and aplasmomycin are described. The syntheses begin with enantioselective epoxidation of 3-buten-2-ol (42) to provide the optically active 2(S),3(R) epoxy alcohol 43. The absolute configuration was confirmed by preparing 43 from (-)-2,3-dihydroxybutyric acid (45). 2,5-Dide- __ oxyribonofuranose (54) and 2,5-dideoxyribono-y-lactone (55) were synthesized from 43. Segments 61 and 39, corresponding to the southeast quadrant of boromycin, and 100 and 107, representing northwest quadrants of aplasmomycin and boromycin, were also prepared from 43. The northeast and southwest quadrants of boromycin and aplasmomycin, 74, were synthesized in optically active form from isobutyraldehyde. Coupling of 74 with 61, followed by modification of functionalities, provided the southern lactone 17 of boromycin. In an intramolecular oxyselenation study for the formation of the tetrahydrofuran ring in the northern segments of boromycin and aplasmomycin, treatment of cis olefinic sulfone 96 with phenylselenyl chloride provided predominantly the 2,5-cis isomer, whereas the trans olefinic sulfone 106 gave the desired 2,5-trans isomer as a major product. The acyl dithiane 129 was prepared from 83, but coupling of this compound with carboimide 131 failed, presumably due to the weak nucleophilicity of the anion of the dithiane. The more reactive 1,3- dithiane 137 was prepared from 124 for the purpose of adding C(1) and C(2) to aplasmomycin.
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  • description.provenance : Approved for entry into archive by Patricia Black(patricia.black@oregonstate.edu) on 2013-07-18T17:53:34Z (GMT) No. of bitstreams: 1 KangMyungC1984.pdf: 917681 bytes, checksum: 2f4077071473b451ff2d7cdb189d5fb0 (MD5)
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