Metalated heterocycles and their applications in synthetic organic chemistry.

The Pd- or Ni-catalyzed cross-coupling reactions of organometals containing Zn, Al, Zr, and B as well as related reactions of Mg and several other metals collectively represent the most widely appl...

Transition Metal-Catalyzed Organometallic Reactions that Have Revolutionized Organic Synthesis

Neurodegenerative diseases and spinal cord injury affect approximately 50 million people worldwide, bringing the total healthcare cost to over 600 billion dollars per year. Nervous system growth factors, that is, neurotrophins, are a potential solution to these disorders, since they could promote nerve regeneration. An average of 500 publications per year attests to the significance of neurotrophins in biomedical sciences and underlines their potential for therapeutic applications. Nonetheless, the poor pharmacokinetic profile of neurotrophins severely restricts their clinical use. On the other hand, small molecules that modulate neurotrophic activity offer a promising therapeutic approach against neurological disorders. Nature has provided an impressive array of natural products that have potent neurotrophic activities. This Review highlights the current synthetic strategies toward these compounds and summarizes their ability to induce neuronal growth and rehabilitation. It is anticipated that neurotrophic natural products could be used not only as starting points in drug design but also as tools to study the next frontier in biomedical sciences: the brain activity map project.

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Neurotrophic Natural Products: Chemistry and Biology

Chemistry and biology of non-tetramic γ-hydroxy-γ-lactams and γ-alkylidene-γ-lactams from natural sources

Hetero-bis-metalated 1,3-butadiene is employed in the lynchpin coupling of synthetic fragments of the side chain of the antitumor agent, lucilactaene. Sequential Stille and Suzuki−Miyaura couplings interpolate this unique boron/tin diene into the pentaene chain. The total synthesis of lucilactaene was accomplished efficiently, in just eight linear steps.

Total synthesis of lucilactaene, a cell cycle inhibitor active in p53-inactive cells.

A convergent total synthesis of epolactaene: an application of the bridgehead oxiranyl anion strategy

Generation and reaction of an oxiranyl anion derived from α,β-epoxy-γ-butyrolactone

Generation and Reaction of an Oxiranyl Anion Derived from α,β‐Epoxy‐γ‐butyrolactone.

The generation and reaction of a lactone-derived oxiranyl anion is described. The aldol-type reaction of the epoxylactone and aldehydes was accomplished by a two-step procedure via the trimethylsilyl epoxylactone. The application of this methodology to the total synthesis of (+)-epolactaene and its analogs is described.

Hideyoshi Itaya

Papers

A convergent total synthesis of epolactaene: an application of the bridgehead oxiranyl anion strategy

Generation and reaction of an oxiranyl anion derived from α,β-epoxy-γ-butyrolactone

Generation and Reaction of an Oxiranyl Anion Derived from α,β‐Epoxy‐γ‐butyrolactone.

A Convergent Total Synthesis of Epolactaene: An Application of the Bridgehead Oxiranyl Anion Strategy.