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oai:null:10339/304282026-09-02T15:05:14Zcom_10339_14934col_10339_38132

Banerjee, Ranjan 2011-02-16T21:42:36Z 2012-12-14T09:30:08Z 2010 https://wakespace.lib.wfu.edu/handle/10339/30428 Hydroxamic acids are an important class of bioactive compounds with wide uses as anti-bacterial, or anti-inflammatory agents and a key component of many natural products, mainly siderophores (low-molecular-weight iron sequestering agents) in lower organisms. Hydroxamic acid based analogs may find potential therapeutic uses in the inhibition of siderophore biosynthesis. Our research targets to develop new synthetic methodology towards making cyclic hydroxamic acids in a stereoselective and regioselective fashion. Basic decomposition of Piloty's acid transforms cyclic ketones (mainly four and five membered) into ring-expanded cyclic hydroxamic acids in 20-69% yield (Scheme 1). Mechanistic study reveals this reaction involves a C-nitroso intermediate 98 (Scheme 47) in the course of the rearrangement, which can also be generated by a separate hydrolysis reaction of acyloxy nitroso intermediate 103 (Scheme 51) leading to the ring-expansion product in 75-80% yield. en Wake Forest University Cobactine and Mycobactic Acid Cyclic Hydroxamic Acid Hydrolysis of five membered ring acyloxy nitroso compound yields hydroxamic acid Intermolecular nitroso-ene method to make linear cyclic and long-chain hydroxamic acid Intramolecular nitroso-ene method to make eight member ring hydroxamic acid -NOH insertion into cyclic ketones in a regioselective and steroselctive fashion DEVELOPMENT OF SYNTHETIC METHODOLOGIES TOWARDS CYCLIC HYDROXAMIC ACID-BASED NATURAL PRODUCTS Dissertation King, Stephen Bruce Garg, Pradeep K Alexander, Rebecca W Colyer, Christa L Jones, Paul B Chemistry 2012-12-14 open.access