Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one of the most important branches of organic chemistry. There are several main areas of research within the general area of organic synthesis: total synthesis, semisynthesis, and methodology.
Bryostatins are a group of macrolide lactones from the marine organism Bugula neritina that were first collected and provided to JL Hartwell’s anticancer drug discovery group at the National Cancer Institute (NCI) by Jack Rudloe. Bryostatins are potent modulators of protein kinase C. They have been studied in clinical trials as anti-cancer agents, as anti-AIDS/HIV agents and in people with Alzheimer's disease.
The Pauson–Khand reaction is a chemical reaction described as a [2+2+1] cycloaddition between an alkyne, an alkene and carbon monoxide to form a α,β-cyclopentenone. The reaction was discovered by Ihsan Ullah Khand (1935-1980), who was working as a postdoctoral associate with Peter Ludwig Pauson (1925–2013) at the University of Strathclyde in Glasgow. The seminal report dates back to 1970, however a detailed follow up was reported in 1973. Initial findings by Pauson and Khand were intermolecular in nature, however many intramolecular examples have been highlighted in both synthesis and methodology reports, starting a decade later from reaction discovery. This reaction was originally mediated by stoichiometric amounts of dicobalt octacarbonyl, but newer versions are both more efficient and catalytic utilizing different chiral auxiliaries for stereo induction, main group transition-metals, and additives to enhance rate of reactivity and yield. For a more extensive review on PKR, refer to Torres' book.
Maitotoxin is an extremely potent toxin produced by Gambierdiscus toxicus, a dinoflagellate species. Maitotoxin is so potent that it has been demonstrated that an intraperitoneal injection of 130 ng/kg was lethal in mice. Maitotoxin was named from the ciguateric fish Ctenochaetus striatus—called "maito" in Tahiti—from which maitotoxin was isolated for the first time. It was later shown that maitotoxin is actually produced by the dinoflagellate Gambierdiscus toxicus.
The Negishi coupling is a widely employed transition metal catalyzed cross-coupling reaction. The reaction couples organic halides or triflates with organozinc compounds, forming carbon-carbon bonds (c-c) in the process. A palladium (0) species is generally utilized as the metal catalyst, though nickel is sometimes used. A variety of nickel catalysts in either Ni0 or NiII oxidation state can be employed in Negishi cross couplings such as Ni(PPh3)4, Ni(acac)2, Ni(COD)2 etc.
Robert S. Coleman is an American chemistry professor and researcher. Coleman was a faculty member at both Ohio State University and the University of South Carolina. At Ohio State, he was on the faculty in the Department of Chemistry from 1996 to 2012, having moved to Ohio State as an associate professor from the University of South Carolina. At USC, Coleman taught as assistant professor from 1989 to 1995, and then as associate professor from 1995 to 1996. In 1996, he accepted a faculty position at Ohio State University to teach Organic Chemistry, where he was an associate professor from 1996 until 2000. He was promoted to full professor in 2000, teaching Organic Chemistry up until his retirement in 2012. He received his Ph.D. degree working with Professor Dale L. Boger, completing the first total synthesis of the antitumor agent CC-1065. He was subsequently an NIH postdoctoral fellow at Yale University with Professor Samuel J. Danishefsky, where he completed, the first total synthesis of the aglycone of the antitumor agent calicheamicin.
Palau'amine is a toxic alkaloid compound synthesized naturally by Stylotella agminata, a species of sea sponge found in the southwest Pacific Ocean. The name of the molecule derives from the island nation of Palau, near which the sponges are found.
Capnellene is a naturally occurring tricyclic hydrocarbon derived from Capnella imbricata, a species of soft coral found in Indonesia. Since the 1970s, capnellene has been targeted for synthesis by numerous investigators due to its stereochemistry, functionality, and the interesting geometry of the carbon skeleton. Many alcohol derivatives of capnellene have demonstrated potential as a chemotherapeutic agent with antibacterial, anti-inflammatory and anti-tumor properties.
Anthony Gerard Martin Barrett FRS, FMedSci is a British chemist, and Sir Derek Barton Professor of Synthesis, Glaxo Professor of Organic Chemistry at Imperial College London. He is Director of the Wolfson Centre for Organic Chemistry in Medical Science. He was elected a fellow of the Royal Society in 1999 and Academy of Medical Sciences in 2003. He obtained a BSc as well as PhD from Imperial College London in 1973 and 1975 respectively.
Velleral (2,2,8-trimethyl-3,3a,8,8a-tetrahydro-1H-azulene-5,6-dicarbaldehyde) is a sesquiterpene dialdehyde found in certain mushrooms, like Lactarius torminosus and Lactarius vellereus, after which it was named. The compound is thought to be part of a chemical defense system that protects the mushrooms against predation. First isolated in 1969, and characterized structurally in 1973, velleral has antimicrobial activity. Several syntheses have been devised.
Stephacidin A and B are antitumor alkaloids isolated from the fungus Aspergillus ochraceus that belong to a class of naturally occurring 2,5-diketopiperazines. This unusual family of fungal metabolites are complex bridged 2,5-diketopiperazine alkaloids that possess a unique bicyclo[2.2.2]diazaoctane core ring system and are constituted mainly from tryptophan, proline, and substituted proline derivatives where the olefinic unit of the isoprene moiety has been formally oxidatively cyclized across the α-carbon atoms of a 2,5-diketopiperazine ring. The molecular architecture of stephacidin B, formally a dimer of avrainvillamide, reveals a complex dimeric prenylated N-hydroxyindole alkaloid that contains 15 rings and 9 stereogenic centers and is one of the most complex indole alkaloids isolated from fungi. Stephacidin B rapidly converts into the electrophilic monomer avrainvillamide in cell culture, and there is evidence that the monomer avrainvillamide interacts with intracellular thiol-containing proteins, most likely by covalent modification.
Biomimetic synthesis is an area of organic chemical synthesis that is specifically biologically inspired. The term encompasses both the testing of a "biogenetic hypothesis" through execution of a series of reactions designed to parallel the proposed biosynthesis, as well as programs of study where a synthetic reaction or reactions aimed at a desired synthetic goal are designed to mimic one or more known enzymic transformations of an established biosynthetic pathway. The earliest generally cited example of a biomimetic synthesis is Sir Robert Robinson's organic synthesis of the alkaloid tropinone.
Atrop-abyssomicin C is a polycyclic polyketide-type natural product that is the atropisomer of abyssomicin C. It is a spirotetronate that belongs to the class of tetronate antibiotics, which includes compounds such as tetronomycin, agglomerin, and chlorothricin. In 2006, the Nicolaou group discovered atrop-abyssomicin C while working on the total synthesis of abyssomicin C. Then in 2007, Süssmuth and co-workers isolated atrop-abyssomicin C from Verrucosispora maris AB-18-032, a marine actinomycete found in sediment of the Japanese sea. They found that atrop-abyssomicin C was the major metabolite produced by this strain, while abyssomicin C was a minor product. The molecule displays antibacterial activity by inhibiting the enzyme PabB, thereby depleting the biosynthesis of p-aminobenzoate.
Bicyclomycin (Bicozamycin) is a broad spectrum antibiotic active against Gram-negative bacteria and the Gram-positive bacterium, Micrococcus luteus that was isolated from Streptomyces sapporonesis and Streptomyces aizumenses in 1972. It belongs to a class of naturally occurring 2,5-diketopiperazines, that are among the most numerous of all the naturally occurring peptide antibiotics. This clinically useful antibiotic is rapidly absorbed in humans when given intramuscularly, has low toxicity and has been used to treat diarrhea in humans and bacterial diarrhea in calves and pigs.
The Krische allylation involves the enantioselective iridium-catalyzed addition of an allyl group to an aldehyde or an alcohol, resulting in the formation of a secondary homoallylic alcohol. The mechanism of the Krische allylation involves primary alcohol dehydrogenation or, when using aldehyde reactants, hydrogen transfer from 2-propanol. Unlike other allylation methods, the Krische allylation avoids the use of preformed allyl metal reagents and enables the direct conversion of primary alcohols to secondary homoallylic alcohols.
In organometallic chemistry, the activation of cyclopropanes by transition metals is a research theme with implications for organic synthesis and homogeneous catalysis. Being highly strained, cyclopropanes are prone to oxidative addition to transition metal complexes. The resulting metallacycles are susceptible to a variety of reactions. These reactions are rare examples of C-C bond activation. The rarity of C-C activation processes has been attributed to Steric effects that protect C-C bonds. Furthermore, the directionality of C-C bonds as compared to C-H bonds makes orbital interaction with transition metals less favorable. Thermodynamically, C-C bond activation is more favored than C-H bond activation as the strength of a typical C-C bond is around 90 kcal per mole while the strength of a typical unactivated C-H bond is around 104 kcal per mole.
Sarah Elizabeth Reisman is a Chemistry Professor at the California Institute of Technology. She received the (2013) Arthur C. Cope Scholar Award and the (2014) Tetrahedron Young Investigator Award for Organic Synthesis. Her research focuses on the total synthesis of complex natural products.
The arylomycins are a class of antibiotics initially isolated from a soil sample obtained in Cape Coast, Ghana. In this initial isolation, two families of closely related arylomycins, A and B, were identified. The family of glycosylated arylomycin C lipopeptides were subsequently isolated from a Streptomyces culture in a screen for inhibitors of bacterial signal peptidase. The initially isolated arylomycins have a limited spectrum of activity against Gram-positive bacteria, including Staphylococcus aureus and Streptococcus pneumoniae. The only activity against Gram-negative bacteria was seen in strains with a compromised outer membrane.
Vinylcyclopropane [5+2] cycloaddition is a type of cycloaddition between a vinylcyclopropane (VCP) and an olefin or alkyne to form a seven-membered ring.
F. Dean Toste is the Gerald E. K. Branch Distinguished Professor of Chemistry at the University of California, Berkeley and Faculty Scientist at the Chemical Sciences Division of Lawrence Berkeley National Lab. He is a prominent figure in the field of organic chemistry and is best known for his contributions to gold chemistry and asymmetric ion-pairing catalysis. Toste was elected a member of the National Academy of Sciences in 2020, and a member of the American Academy of Arts and Sciences in 2018.
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