https://pubs.rsc.org/en/content/articlepdf/2019/NP/C8NP00092A

Marine natural products.

https://www.erowid.org/archive/rhodium/pdf/suzuki.cross-coupling.review.1995-1998.pdf

Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles, 1995–1998

Isoflavonoids of the leguminosae

IL-18, a cytokine originally identified as IFN-gamma-inducing factor, is a member of the IL-1 family of proteins. Because IL-1alpha and IL-1beta are important mediators in the pathogenesis of arthritis, the present study addresses the expression of IL-18 and its role in regulating in articular chondrocytes. IL-18 mRNA was induced by IL-1beta in chondrocytes. Chondrocytes produced the IL-18 precursor and in response to IL-1 stimulation secreted the mature form of IL-18. Studies on IL-18 effects on chondrocytes showed that it inhibits TGF-beta-induced proliferation and enhances nitric oxide production. IL-18 stimulated the expression of several genes in normal human articular chondrocytes including inducible nitric oxide synthase, inducible cyclooxygenase, IL-6, and stromelysin. Gene expression was associated with the synthesis of the corresponding proteins. Treatment of normal human articular cartilage with IL-18 increased the release of glycosaminoglycans. These finding identify IL-18 as a cytokine that regulates chondrocyte responses and contributes to cartilage degradation.

IL-18 Is Produced by Articular Chondrocytes and Induces Proinflammatory and Catabolic Responses

Transmetalation of Unsaturated Carbon Nucleophiles from Boron-Containing Species to the Mid to Late d-Block Metals of Relevance to Catalytic C−X Coupling Reactions (X = C, F, N, O, Pb, S, Se, Te)

Isoflavonoids and related compounds

Palladium-catalysed coupling of the 4-chloro- or 4-bromo-coumarins 1–4 with arylboronic acids 5–13 under the Suzuki reaction conditions constitutes an efficient access to 4-arylcoumarins. These 4-arylcoumarins can also be obtained in good yields (70–97%) by treatment of 4-trifluoromethyl-sulfonyloxycoumarins 35–38 with arylboronic acids under modified Suzuki reaction conditions, involving the use of copper(I) iodide as a co-catalyst.

Synthesis of neoflavones by Suzuki arylation of 4-substituted coumarins

1996. The format follows the pattern of its predecessor, 1 with an emphasis on the isolation and synthesis of new members of the isoflavonoid family. Although the distribution of isoflavonoids among plants is relatively sparse they nevertheless form a large and very distinctive subclass of the flavonoid family with a wide variety of structural variations encountered in nature. Continued interest in the isolation of new isoflavonoids arises due to the diverse range of biological activities including antimicrobial, oestrogenic and insecticidal activities which they possess. The pharmacological properties of isoflavonoids have been reported, especially papers detailing the relationship between consumption of isoflavonoids and reduction in the incidence of cardiovascular disease and cancer but these will not be discussed in this report. It is interesting to note that there has been a slight decrease in the number of new isoflavones isolated during this review period. While this may be a temporary slow down in productivity, it may also indicate that new compounds are becoming harder to find. It is significant that several new isoflavonoid oligomers are now reported (Section 8), as the existence of natural isoflavonoid oligomers has only recently been confirmed. 2 These new compounds comprising of isoflavonoid units linked to other isoflavonoid and neoflavonoid units complement the rare series of isoflavonoids linked to flavonoid, stilbene and phenylpropanoid units. In addition to this report two further papers detailing isoflavonoids from African plant species 3 and the chemical and biological aspects of isoprenoid substituted isoflavonoids 4 have been published.

Isoflavonoids and Related Compounds

Practical total syntheses of axinastatins 2 2b and 3 2c were completed by employing Fmoc protection for the N-terminal, and tert-butyl ester blocking for the C-terminal, units of the amino acid and peptide intermediates. Generally, diethyl phosphorocyanidate proved effective for formation of the peptide bond, and in the one exception, asparagine, the o-nitrophenyl active ester proved to be useful. For the final cyclization reaction BOP-Cl was found especially effective.

Gerard M. Boland

Papers

Isoflavonoids and related compounds

Synthesis of neoflavones by Suzuki arylation of 4-substituted coumarins

Isoflavonoids and Related Compounds

Synthesis of the cyclic heptapeptides axinastatin 2 and axinastatin 3

Antineoplastic Agents. Part 343. Synthesis of the Cyclic Heptapeptides Axinastatin 2 and Axinastatin 3