From the root bark of Aspidospermmegalocarpon Muell. Arg. a new alkaloid, aspidocarpine, has been isolated. It has the empirical formula C22H30O3N2 and contains an N-acetyl, one methoxyl group, and one active hydrogen. The alkaloid, a phenolic monoacidic tertiary base, has been shown by its properties, those of its derivatives, and the spectroscopic data, to contain an N-acetyl-6-methoxy-7-hydroxydihydroindole moiety. Oxidation of aspidocarpine with chromic acid gave rise to a product identical in all respects with apoaspidospermine obtained from the similar oxidation of aspidospermine. Since the structure of aspidospermine is known, the foregoing results establish the structure of the alkaloid aspidocarpine.

Isolation and structure of a new alkaloid: aspidocarpine

Synthesis of 2,6-diaryl-3-(trifluoromethyl)pyridines by regioselective Suzuki–Miyaura reactions of 2,6-dichloro-3-(trifluoromethyl)pyridine

Trifluoromethyl-substituted 1,3-diketones can undergo direct alkynylation reactions which are not possible for alkyl- or aryl-substituted derivatives. The products can be easily transformed into 2,6-diaryl-4-trifluoromethylpyridines by acid-mediated [5+1] cyclization with urea. The reaction was thoroughly optimized by variation of the conditions and the scope was studied in detail. The products are not readily available by other methods. A plausible mechanism was suggested based on DFT calculations.

Synthesis of 4-Trifluoromethylpyridines by [5+1] Cyclization of 3-Hydroxy-pent-4-yn-1-ones with Urea

Gegen Malaria wirksame 6-Aminochinoline, V. 2-, 3- und 4-Mono-, Di- und Trimethylderivate von 6-(4-Diäthylamino-1-methylbutylamino)-5,8-dimethoxychinolin

William Henry Perkin, Jr. FRS, the son of the inventor of mauve and other commercial dyes and credited for initiating the industrialization of chemistry, was himself a notable chemist. He was the Professor of Organic Chemistry at Manchester from 1892-1912 and then was the Waynflete Professor of Chemistry at Oxford and the first Head of the Dyson Perrins Laboratory from 1912-1929. One of Perkin's graduate students and research assistants at Manchester was Robert Robinson, subsequently Sir Robert Robinson, FRS and recipient of the 1947 Nobel Prize in Chemistry. Perkin and Robinson had perhaps the most productive and broad collaboration between a professor and one's student. Together, during and after Robinson's student days, they had 71 joint publications, 25 of which involved just the two of them, 17 of which involved the structure determination of strychnine, and eight of which were published after Perkin's death in 1929. Upon Perkin's early death, Robinson succeeded him as the fourth Waynflete Professor of Chemistry at the Dyson Perrins Laboratory, Oxford University. This Essay will examine the professional relationship of Perkin, Jr. and Robinson as revealed in their joint publications on the structure of strychnine.

Francis Lions

Papers

CLXI.—Strychnine and brucine. Part III. The position of the methoxyl groups in brucine