ORGN 901 |
| Diversity oriented synthesis is a highly economical approach leading to skeletally diverse scaffolds. Even though DOS was described for natural products, this strategy was frequently used from the beginning of the combinatorial synthesis in the formation of various heterocyclic scaffolds. The piperidine moiety is recognized among numerous GPCR-antagonist privileged structures and these compounds exhibit various biological activities including antihypertensives, narcotic analgesics and digestive system drugs. 4-Piperidones are frequently used precursors of several spiro-ring systems reacting with present or in situ generated 1,4-bifunctional moieties. Piperidine fused heteroaromatic scaffolds can be synthesized directly from 4-piperidones using either the acidic alpha CH2 in enolate addition reaction or the carbonyl moiety in condensation reaction followed by ring-closure. Moreover, 3-carbethoxy-4-piperidones are frequently used alternatives as bifunctional BBs for heterocyclic ring formation. In this lecture we describe the versatile synthesis of piperidine-based heterocycles from their adaptation to parallel synthesis up to realized combinatorial libraries.
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Combinatorial, Parallel, and Solid-Phase Chemistry
8:00 AM-12:00 PM, Thursday, 14 September 2006 Moscone Center -- Room 132, Oral
Division of Organic Chemistry |
