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Total Synthesis of CP Compounds

Man's fascination with the many uses that can be found with the exploitation of natural substances has been demonstrated time and again throughout history, but the stage was set at the turn of the century for organic chemists to begin to focus on utilizing natural compounds for the benefit of medicinal and industrial uses. The discoveries of penicillin, aspirin, and other naturally occurring useful compounds in the earlier parts of the century set the stage for the utilization and exploitation of biologically active compounds as a molecular science.However, there are limits as to how much we can do with what nature provides us. This puts the role of the synthetic organic chemist at the forefront of synthetic compound synthesis technology. KC Nicolaou is one such leader.The main goal of Nicolaou's lab is the complete synthesis of naturally occurring compounds, along with solid phase chemistry, molecular design, combinatorial synthesis, and biological investigations; some of the results of Nicolaou's work include: the total synthesis of the anticancer agent Toxol, the marine neurotoxins brevetoxins A and B, the anititumor agents epothilones A and B, eleutherobin and sarcodictyins, the antibiotic vancomycin, the cholesterol-lowering CP-molecules, the immunosuppressant agent sanglifehrin A, the antibiotic everninomicin, and a number of bisorbicillinoids such as trichodimerol, bisorbicillinol, and bisorbibutenolide.Another example of Dr. Nicolaou's work is a paper published in Chemistry International entitled The Absolute Configuration and Asymmetric Total Synthesis of the CP Molecules (co-authored by Jae-Kyu Jung, Won Hyung Yoon, Yun He, Yong-Li Zhong, and Phil Baran.) In this paper, Nicolaou and his associates describe how their goal was both the total synthesis of these CP compounds (achieved in 1999) along with the determination of their absolute configurations; methods used in initial attempts to determine absolute configuration a...

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