DEVELOPMENT OF SYNTHETIC METHODOLOGIES TOWARDS CYCLIC HYDROXAMIC ACID-BASED NATURAL PRODUCTS

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.

Grantor dc:publisher

Wake Forest University

Year dc:date.issued

2010

Author dc:creator

• Banerjee, Ranjan

• Cobactine and Mycobactic Acid

Language dc:language.iso

en

Handle dc:identifier.uri

http://hdl.handle.net/10339/30428

OAI identifier oai:identifier

oai:wakespace.lib.wfu.edu:10339/30428