Stitching With Nitrogen

来源 :2005 WHTS'3rd Annual Congress of International Drug Discove | 被引量 : 0次 | 上传用户:cgrong
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  Molecules produced by the living systems have always inspired synthetic organic chemists.With the fields of organic and medicinal chemistry evolving as they did from a desire to explore and learn from the chemistry of life, the practitioners of these disciplines have naturally favored using reactions which are similar to the prototypical biosynthetic pathways.As a consequence, todays favorite targets, both in academic and industrial pharmaceutical chemistry laboratories, are some of the most complex natural substances ever discovered.Lacking her exquisite and complex stratagems to steer this essentially thermoneutral chemistry, synthetic organic chemists have learned to rely on such highly reactive agents as organolithiums and enolates.Thus, modem organic synthesis depends heavily on inertatmospheres and dry solvents to support the use of these extremely basic and/or acidic species, requiring that most heteroatom functionality in turn be protected and protic solvents are avoided.A heavy price is therefore exacted when the goal is to synthesize the extensive carboncarbon bond frameworks found in many natural products.Fortunately, the universe of possible small molecule drug candidates remains virtually unexplored: the ratio of synthesized to reasonably possible structures is roughly the same as the mass of a proton is to the mass of the sun.With this kind of structure space available, we propose a synthetic strategy which relies upon heteroatom-carbon bond connections and the use of at least one relatively high-energy, "spring-loaded" component, making the bond-forming processes Pre programmed and exergonic.New molecules of dazzling complexity can arise from very short reaction sequences between spring-loaded blocks which become permanently united together via heteroatoms.We begin with nitrogen, which is second onlu to carbon in its connectivity potential in orgaic chemistry.
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