Laura C. Paterson

Tuned methods for conjugate addition to a vinyl oxadiazole; synthesis of pharmaceutically important motifs

The addition of various nucleophiles to a vinyl 1,2,4-oxadiazole is described. Following optimisation, individual protocols tuned for the use of each specific class of reagent have been developed to allow the installation of nitrogen, sulfur, oxygen, and carbon nucleophiles, and leading to the preparation of a series of compounds containing the pharmaceutically important oxadiazole motif.

Iridium(I)-catalyzed Regioselective C-H Activation and Hydrogen Isotope Exchange of Non-aromatic Unsaturated Functionality

Isotopic labelling is a key technology of increasing importance for the investigation of new CH activation and functionalization techniques, as well as in the construction of labelled molecules for use within both organic synthesis and drug discovery. Herein, we report for the first time selective iridium-catalyzed CH activation and hydrogen-isotope exchange at the β-position of unsaturated organic compounds. The use of our highly active [Ir(cod)(IMes)(PPh3 )][PF6 ] (cod=1,5-cyclooctadiene) catalyst, under mild reaction conditions, allows the regioselective β-activation and labelling of a range of α,β-unsaturated compounds with differing steric and electronic properties. This new process delivers high levels of isotope incorporation over short reaction times by using low levels of catalyst loading.

Executing Scottish Witches

The sayde Doctor Fian was soone after araigned, condemned, and adjudged by the law to die, and then to bee burned according to the lawe of that lande, provided in that behalfe. Whereupon hee was put into a carte, and beeing first strangle d, hee was immediatly put into a great fire, being readie provided for that purpose, and there burned in the Castle hill of Edenbrough on a Saterdaie in the ende of Januarie lastpast, 1591.1

A tetrahydropentaleno[1,6a-a]naphthalen-4(2H)-one of defined relative stereochemistry for use towards Agariblazeispirol C

Towards the synthesis of the novel natural product Agariblazeispirol C, (5aR*,11bR*)-9-methoxy-3,8,11b-trimethyl-5,6,7,11b-tetrahydro-1H-pentaleno[1,6a-a]naphthalen-4(2H)-one, C(20)H(24)O(2), has been prepared at a key stage of the preparative programme. The structure shows the desired stereochemical outcome of the central cyclization protocol, viz. a syn-relationship between the aliphatic methyl group on the 11b-position and the methylene group on the 5a-position [C-C-C-C = -34.57 (18) degrees ].