Anne-Marie Lamidey

Highly Diastereoselective Synthesis of Orthoquinone Monoketals through λ3-Iodane-Mediated Oxidative Dearomatization of Phenols†

Orthoquinone monoketals A and orthoquinols B are cyclohexa-2,4-dienone derivatives with valuable reactivity features for the construction of complex molecular architectures. Their conjugated dienone unit and the vicinal positioning of their oxygenated functionalities constitute a unique structural arrangement that can be transformed rapidly into various kinds of polyoxygenated (poly)cyclic systems (Scheme 1).

Payne-like rearrangement of N-tosyl-oxiranemethylamines : a new route to functionalized aziridines

Abstract The reaction of N-tosly-oxiranemethylamines with aqueous sodium hydroxide affords N-tosyl-aziridinemethanols in excellent yields, through the intramolecular epoxide ring opening by the nitrogen atom of the tosylamino group.

A PRACTICAL SYNTHESIS OF AMBROX® FROM SCLAREOL USING NO METALLIC OXIDANT

The commercial synthesis of Ambrox® is modified so that the key intermediate, the sclareolide, results from an indirect oxidative degradation of sclareol. This method allows to greatly alleviate the waste disposal problem and to raise the overall yield of Ambrox® to 75%.

A convenient synthesis of the Echinacea-derived immunostimulator and HIV-1 integrase inhibitor (-)-(2R, 3R)-chicoric acid

The Echinacea-derived immunostimulator and HIV-1 integrase inhibitor (−)-chicoric acid (=2,3-bis{[3-(3,4-dihydroxyphenyl)-1-oxoprop-2-enyl]oxy}butanedioic acid; 1a) was conveniently prepared via a silane-promoted Pd-mediated chemoselective hydrogenolysis of its perbenzylated derivative 12a, which was generated from an efficient and reliable carbodiimide-mediated coupling reaction between the caffeic acid dibenzyl ether derivative 7 and commercially available (+)-dibenzyl L-tartrate (9a). The other naturally occurring dextrorotatory chicoric acid (1b) can be similarly prepared.

Phase-Transfer Catalytic Alkylation of Hydroperoxides: A Convenient Route to Mixed Dialkyl Peroxides

Abstract The solid-liquid phase transfer catalytic alkylation of hydroperoxides using solid potassium hydroxide as a base and TEBAC as a phase transfer catalyst is reported. When the alkylating agent is a primary bromide, this reaction represents a simple and quick method for the synthesis of mixed dialkyl peroxides in fair yields.

Substituent control in the synthesis of azetidines and pyrrolidines by N-tosyl-oxiraneethylamines base-mediated cyclization

Abstract N-tosyl-oxiraneethylamines undergo cyclization upon treatment with aqueous sodium hydroxide to afford either N-tosyl-azetidinemethanols or N-tosyl-pyrrolidin-3-ols in high yields. The change in regioselectivity of this cyclization process is quite dependent on the location of a pentamethylene substitution in the chain connecting the nitrogen with the oxirane ring.

A Short and Efficient Synthesis of (+)-13-Epimanoyl Oxide from Sclareol

Abstract (+)-13-Epimanoyl oxide has been synthesised in four steps from natural sclareol in an overall yield of 78%; preparation of the related labdane-14,15-diols is involved in this synthetic pathway.