10.1016/0039-128X(81)90038-6
The research focuses on the total synthesis of 12,15-bisthia-1,3,5(10),6,8,13(14)-gonahexaen-17-one (III), a heterocyclic steroid compound. The study aims to explore the influence of sulfur at position '12' of the steroid nucleus on biological activity, building on previous work on 3-deoxy-12-thiaequilenin and 12-thiaequilenin methyl ether. The synthesis involves a series of chemical reactions starting with 1-chloromethylnaphthalene (IV), which is treated with thioglycollic acid in sodium hydroxide to form l-naphthylmethyl-thioacetic acid (V). This compound is then cyclodehydrated with phosphorus pentoxide to yield 1-oxo-3-thia-1,2,3,4-tetrahydrophenanthrene (VI). Further reactions with thioglycollic acid and p-toluenesulfonic acid (PTS) lead to the formation of (3-thia-3,4-dihydrophenanthren-1-yl)thioacetic acid (VII), which is cyclodehydrated again to obtain the target compound (III).
10.1021/jo960103t
2-Methoxypropionic acid (O-methyllactic acid, 1) is a carboxylic acid with a methoxy group attached to the second carbon atom of the propane chain. It is liquid at room temperature and soluble in organic solvents such as methanesulfonic acid and polyphosphoric acid. It is the main reactant in this study. The methoxy and carboxyl groups are essential to the reaction mechanism that ultimately produces 1,1-diarylethane. Phosphorus pentoxide (P2O5) is a compound with the molecular formula P2O5. It is a white crystalline solid that is highly hygroscopic and reacts violently with water to produce phosphoric acid. It acts as a dehydrating agent and a strong acid catalyst in the reaction mixture. It is essential for the oxidative decarboxylation step. The research demonstrates a novel tandem diarylation reaction that selectively forms 1,1-diarylethanes from 2-methoxypropanoic acid in the presence of P2O5-MeSO3H. The reaction shows specific substrate requirements and is influenced by the nucleophilic character of the aromatic compounds used.