Theses and Dissertations at Montana State University (MSU)
Permanent URI for this collectionhttps://scholarworks.montana.edu/handle/1/733
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Item Synthetic routes to perhydroazulenes; studies with oxygenated models(Montana State University - Bozeman, College of Letters & Science, 1971) DeBernardis, Amo RichardItem Fused small ring compounds(Montana State University - Bozeman, College of Engineering, 1960) Yao, Shi-KuangItem Complexes of 1, 8-naphthyridines with elements of the first transition series(Montana State University - Bozeman, College of Letters & Science, 1971) Emad, AhmadItem Studies toward the total synthesis of scytophycin C : sythesis of the C(1)-C(18) fragment(Montana State University - Bozeman, College of Letters & Science, 2004) Harney, Michael John; Chairperson, Graduate Committee: Paul A. GriecoThe goal of this investigation was to provide a synthetic route to the C(1) - C(18) fragment of scytophysin C 5 which would be amenable to large scale preparation of the target compound. To achieve this goal it would be necessary to circumvent the problems encountered in Grieco and Speakers aforementioned synthesis. These problems were namely the reduction of the nitrile at C(14) in the presence of the C(1) carboxymethyl group and the protecting group manipulations which were necessitated by the alternate homologation strategy which was employed. Synthetic Strategy In order to avoid possible interference resulting from the presence of the C(I) carbomethoxy group during the reduction of the C(14) nitrile it was decided to delay introduction of the C(1) - C(6) portion of the molecule until the last steps of the synthesis. Therefore, it would be necessary to reduce the C(7) aldehyde product of the Ferrier rearrangement and subsequently protect the resultant alcohol. Provided the reduction of the C(14) nitrile was a success the C(15) - C(18) portion of the molecule could then be installed using Roush’s (S,S) diisopropyltartrate-Z-crotylboronate. Finally, the C(1) - C(6) portion of the molecule could be elaborated by deprotection and oxidation of the C(7) alcohol to it’s corresponding aldehyde followed by a vinylogous Muldyama type aldol reaction, Homer-Emmons olefmation, and protection of the C(7) alcohol as its tert-butyldimethylsilyl ether. It was thought that this route, if feasible, would result in a significantly shorter and more efficient synthesis of 5.Item The synthesis of 2-methyl butanal by reaction of n-butyl isocyanide with secondary-butylcadmium bromide, pt. 1 : a study of the reactions between carbon monoxide and the sodium salt of nitroethane, pt. 2(Montana State University - Bozeman, College of Letters & Science, 1949) Bruce, John M.Item New approaches to natural products(Montana State University - Bozeman, College of Letters & Science, 1985) Jun, Jong-GabItem Studies directed toward the synthesis of the C(19)-C(32) carbon fragment of Scytophycin C(Montana State University - Bozeman, College of Letters & Science, 2002) Swain, William RichardItem New synthetic methodologies for natural products(Montana State University - Bozeman, College of Letters & Science, 1978) Bornmann, William GerardItem Studies on pinacol chemistry(Montana State University - Bozeman, College of Letters & Science, 1985) Bruss, Dan R.Item Study on the molecular rearrangements and synthesis of natural products(Montana State University - Bozeman, College of Letters & Science, 1982) Kim, Youseung