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Bromonium-Initiated Epoxide-Opening Cascades : total Synthesis of ent-Dioxepandehydrothyrsiferol and Synthetic Studies toward (+)-Scholarisine A
(Massachusetts Institute of Technology, 2013)
CHAPTER I. Bromonium-Initiated Epoxide-Opening Cascades: Total Synthesis of ent-Dioxepandehydrothyrsiferol Our foray into the total synthesis of ent-dioxepandehydrothyrsiferol has led to the discovery and development of ...
Nickel-catalyzed cross-couplings of unactivated secondary and tertiary alkyl halides and photoinduced copper-mediated asymmetric C-N cross-couplings
(Massachusetts Institute of Technology, 2013)
Chapter 1 describes the development of two nickel-catalyzed Suzuki cross-coupling methodologies that employ alkyl halides as electrophiles. In Section 1.1, asymmetric [gamma]-alkylation relative to a carbonyl group is ...
Enantioselective total Synthesis of the agelastatin and trigonoliimine alkaloids
(Massachusetts Institute of Technology, 2012)
I. Total Synthesis of the (-)-Agelastatin Alkaloids The pyrrole-imidazole family of marine alkaloids, derived from linear clathrodin-like precursors, constitutes a diverse array of structurally complex natural products. ...
Direct dehydrative N-Pyridinylation of amides, the interrupted Bischler-Napieralski reaction, and the enantioselective total synthesis and arylative dimerization of aspidosperma alkaloids
(Massachusetts Institute of Technology, 2013)
I. Direct Dehydrative N-Pyridinylation of Amides A method for the single-step N-pyridinylation of secondary amides is described. The process involves electrophilic activation of secondary amides with trifluoromethanesulfonic ...
Carbon-trifluoromethyl bond forming reactions and palladium-catalyzed cyanation of (hetero)aryl halides
(Massachusetts Institute of Technology, 2013)
Chapter 1 Nucleophilic trifluoromethyl sources were systematically examined in stoichiometric palladium experiments to determine the most efficient class of reagents for transmetallation. In conjunction with reductive ...
Development of novel transition metal-catalyzed cross-coupling reactions and applications thereof
(Massachusetts Institute of Technology, 2013)
Chapter 1 The first example of Pd(0)/(II) catalyzed fluorination of aryl bromides is reported herein. Based on these data, an analogous method was developed for the fluorination of aryl triflates. The reaction proceeds ...
Total synthesis of cyclotryptamine and diketopiperazine alkaloids
(Massachusetts Institute of Technology, 2013)
I. Total Synthesis of the (+)-12,12'-Dideoxyverticillin A The fungal metabolite (+)-12,12'-dideoxyverticillin A, a cytotoxic alkaloid isolated from a marine Penicillium sp., belongs to a fascinating family of densely ...