A palladium catalyzed coupling reaction of an organotin reagent bearing acrylate functionality with an acid chloride serves as a method to introduce both a ketone and an acrylate functionality into a carbon framework; thus the coupling reaction of 4-t-butyldiphenylsiloxypentanoyl chloride with b...

Naphthenic acids (NAs) originate from bitumen and are considered a major contributor to acute toxicity in oil sands process-affected water (OSPW) produced from bitumen extraction processes. To reclaim oil sands tailings and remediate OSPW, in-pit fluid fine tailings can be water-capped as end pi...

A combination of triphenylphosphine (PPh3) and 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) provides a safe and easily available mixed reagent system for the conversion of 1° and 2° alcohols, thiols, trimethylsilyl-, and tetrahydropyranyl ethers to their corresponding thiocyanates and the 3° on...

An efficient one-pot cascade methodology for the synthesis of (ethoxycarbonyl)difluoromethyl thioethers is described. Benzyl, allyl, alkyl halides or diazonium salts as the starting materials together with thiocyanate sodium and TMS-CF2CO2Et in the presence of CsF or NaOAc afford a variety of th...

Aerobic intramolecular aminothiocyanation of unactivated alkenes has been developed by in situ generated iodine thiocyanate under open-flask conditions. This protocol provides a concise and efficient method for synthesizing SCN-containing pyrrolidine, piperidine and indoline derivatives with iso...

The trifluoromethylation of aldehydes and ketones is a potentially powerful method to introduce the CF3 moiety into organic molecules. In general, the trifluoromethylation reaction has been performed by treatment of Me3SiCF3 under initiation by TBAF, TBAT, TMAF as well as CsF. However, these com...

Acetonylation of α,β-enones can be achieved by reactions either with (2-methyl-2-propenyl)trimethylsilane or with allyltrimethylsilane followed by oxidative cleavage of the double bond or by the Wacker reaction, respectively. Annelation of the 1,5-diketones is also described briefly.

The lithium enolate of trimethylsilyl acetate (1) undergoes a 1,3-O → C migration of the trimethylsilyl group.

Unsaturated spiro-γ butyrolactones can be prepared in good yields from bromoacetate precursors by a simple route that requires only 2-propanol as solvent and free radical initiation.

Treatment of (2-hydroxyprop-2-yl)diphenylphosphine oxide with silylating agents affords trimethylsilyl diphenylphos-phinite in high yield.

A simple way of synthesising 2-(arylamino)ethyl phosphonic esters and acids via the aza-Michael addition of amines to diethyl vinylphoshonate ‘on water’ was developed. Various 2-(arylamino)ethyl phosphonates were initially produced through the condensation of primary and secondary amines with ...

5′-(E)-Vinylphosphonate (VP) is an effective bioisostere of the natural 5′-monophosphate in small interfering RNAs (siRNAs). Solid-phase synthesis of VP-siRNAs requires the use of appropriately protected VP-phosphoramidites in combination with optimal oligonucleotide deprotection conditions. A...

ObjectiveTo determine the effect of a popular oral contraceptive, l-norgestrel (a synthetic progestogen), on relaxing response of clitoral cavernous smooth muscles.

The aim of this study was to investigate the effects of progestins on the hypothalamic–pituitary–thyroid (HPT) axis in the early stage of zebrafish. Zebrafish embryos were exposed to progesterone (P4) or norgestrel (NGT) at 5, 50 and 100 ng L− 1 for 144 h post fertilization (hpf), and the tran...

The aim of this study was to investigate the effects of progestins on the sex differentiation of zebrafish by measuring the sex ratio and transcriptions of genes related to sex differentiation (Amh, Dmrt1, Figa, Sox9a and Sox9b genes) as well as sex hormone levels and transcriptional expression ...

Single intragastric 0.5 mg/kg doses of 14C-d-norgestrel-3-oxime-17-acetate were given to female rhesus monkeys. Rapid absorption was evidenced by peak concentrations of radioactivity in plasma and whole blood within three hours. A multiphasic decline in concentrations of radioactivity then follo...

Synthetic estrogens and progestins are commonly used in human and veterinary medicine. After use, they reach aquatic environments via discharge of wastewaters from human and animals, thus posing potential risks to organisms. So far, very little is known about their combined effects in aquatic or...

The relationship between the transdermal flux through hairless mouse skin of a solute (d-norgestrel) and two solvents (ethanol and ethyl acetate) at apparent steady state was studied using irreversible thermodynamics. To accomplish this, a model was developed based on the linear relationship bet...

Medroxyprogesterone acetate (MPA) is a widely used synthetic progestin and it has been frequently detected in aquatic environments. However, its effects on aquatic organisms remain largely unknown. Here we investigated the chronic effects of MPA on sex differentiation and gonad development in ze...

Natural and synthetic steroid hormones such as progesterone and norgestrel in the aquatic environment may cause adverse effects on aquatic organisms. This study investigated the biotransformation of progesterone and norgestrel in aqueous solutions by two freshwater microalgae Scenedesmus obliquu...