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Creator:: Choi, Younggi
Abstract:: PART I. The preparation of (-)-ibogamine (1) in fourteen steps from benzoquinone and in 10% overall yield is a powerful illustration of the value of the asymmetric Diels-Alder reaction as a starting point in a multistep synthesis. All four cycloadducts, 70, 77, 84 and 96, obtained with the (S)-BINOL-TiCl₂ complex...
Resource Type:: Dissertation
Full Text:: indolization. 0TH P 0 1. LAH, 91% OTHP 0TH P 2. Hg(OAc)2, 80% o - 2. N2H4 OEt 60% from 23 Et 22 23 24

Creator:: Sundermann, Kurt F.
Abstract:: A convergent synthesis of epothilone B that generates all seven of its asymmetric centers in a completely stereoselective fashion has been completed. Key reactions include an anti-Felkin aldol condensation to set the C6 and C7 stereochemistry, a directed α-hydroxylation to install the C15 (S)-hydroxyl substituent, and a Wittig condensation to...
Resource Type:: Dissertation
Full Text:: -sensitive and multidrug-resistant cells that overexpress the P-glycoprotein efflux pump.1° Heterodimer

Creator:: Shanmugham, Meenakshi Sundaram
Abstract:: Two approaches to the tricyclic core of the furanoeremophilane sesquiterpenoids are described. The first approach entails a projected Diels-Alder/retro Diels-Alder reaction of an acetylenic oxazole 64. Construction of the pivotal aldehyde 67 commenced from ketone 68. The acetyenic moiety was then introduced via a Felkin-Ahn addition of lithiopropyne to aldehyde...
Resource Type:: Dissertation
Full Text:: ketoacid with p-toluenesulfonic acid in refluxing toluene furnished (±)-1 1- desmethyleremophilenolide 29

Creator:: Wang, Guoqiang
Abstract:: Studies towards the total synthesis of (-)-gymnodimine (1), a marine neurotoxin with a unique molecular architecture and pronounced biological activity, are described. These studies resulted in a convergent approach to the advanced intermediate 315, containing the C3-C32 section of 1. Two synthetic routes were developed to construct the tetrahydrofuran subunit...
Resource Type:: Dissertation
Full Text:: ............................................................4 1.3 Gymnodamine and its p-Bromobenzamide Derivative ...................................5 1.4

Creator:: Lincoln, Christopher M.
Abstract:: The rearrangement of a homoallyl cation to a cyclopropylcarbinyl cation is thought to play a role in the biogenesis of a variety of cyclopropane-containing natural products,¹ a hypothesis which has previously led to the design of successful biomimetic syntheses of several natural products.² The strategy underlying this approach to cyclopropane...
Resource Type:: Dissertation
Full Text:: Foundation and D. P. Shoemaker are thanked for financial support. I would also like to thank my wife Laura

Creator:: Smits, Helmars
Abstract:: Studies towards the total synthesis of (−)-kendomycin (1), a bacterial metabolite with a unique molecular architecture and pronounced biological activity, are described. These studies resulted in the synthesis of advanced intermediate 208, containing all of the carbon atoms of 1. A Dötz annulation between alkyne 122 and novel chromium carbenoid...
Resource Type:: Dissertation
Full Text:: ) p-TsNHNH2, EtOH, 4A MS, reflux 2) NaCNBH3, ZnCl2, EtOH reflux, 65% OMe OMe OMe MeO O HO

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