Sumários
Synthesis of Isocomene (Pirrung)
7 Dezembro 2016, 14:00 • Christopher David Maycock
1,3-diones and their alkylation. Preparation of 2-methylcyclohexane-1,3-dione. Formation of a vinyl ether by an addition elimination reaction or via substitution of a chloride. Methods for the remote alkylation of 1,3-diones and beta-ketoesters. alfa-Alkylations of ketones in general. Reaction of alf-beta-unsaturated ketones with organometallic reagents (1,2- versus 1,4-addition) Use of copper reagents for 1,4-additions.1,2-additions with Mg reagents. Acid hydrolysis of vinyl ethers and elimination of water from beta-hydroxyketones. Intramolecular [2+2]-cycloadditions using UV-light. Conformation of transition states and the stereochemical outcome of reactions.
Synthesis of 2-chloro-5-iodopyridine (PL11.1)
30 Novembro 2016, 16:00 • Christopher David Maycock
Diazotisation of 2-amino-5-iodopyridine using sodium nitrite in HCl.
Synthesis of AI-2 (1,2-Dihydroxypentane-3,4-dione, DPD)
30 Novembro 2016, 14:00 • Christopher David Maycock
AI-2 (Autoinducer 2) is a quorum sensing molecule for interspecies bacterial communication. It is simple optically pure molecule that exists in several cylic and hydrated forms.
Similar routes can be used for forming the unlabelled compound or the 1- or 2- 13C-labelled compounds.
Synthesis of 2-amino-5-iodopyridine
23 Novembro 2016, 16:00 • Christopher David Maycock
Selective iodination of 2-aminopyridine in the 5-position using iodine in acetic acid.
Synthesis of part of Erythronolide B (Corey)
23 Novembro 2016, 14:00 • Christopher David Maycock
Starting from 2,4,6-trimethylphenol.
Alkylation in the 4-position to produce a non-aromatic symmetrical unaturated ketone that allows bidirectional functionalisation.