10.1016/S0040-4020(97)10136-3
The study investigates two methods for reducing ketene dithioacetals to produce substituted dithianes, which serve as building blocks for heterocyclic synthesis. The researchers, John M. Mellor, Stephen R. Schofield, and Stewart R. Korn, compared the effectiveness of magnesium in methanol and zinc in acetic acid for this reduction process. They found that zinc in acetic acid was more reliable than magnesium in methanol, which showed inconsistent results due to steric constraints in certain substrates. The study also involved the preparation of various ketene dithioacetals using two methods: reaction of carbon disulfide with the enolate anion of appropriate 1,3-dicarbonyl compounds in dimethylformamide or on alumina. The resulting dithianes were then successfully converted into heterocyclic aldehydes through cyclization and deprotection steps, demonstrating their utility in synthesizing complex heterocyclic structures.
10.1021/jo010703e
The study describes a practical synthesis of a second-generation benzoin photolabile safety-catch (BPSC) linker for solid-phase organic synthesis (SPOS). The new linker, featuring a carboxylic acid functionality for resin attachment and a four-carbon tether for enhanced stability, can be loaded onto amine-terminating resins or preloaded with substrates in solution before resin immobilization. This approach offers improved control over linker loading and substrate attachment, making it versatile for SPOS applications. The research highlights the synthesis process, resin attachment, and photolytic cleavage efficiency, demonstrating the linker's potential utility in complex organic synthesis.
10.1021/ol201426c
The research aims to develop an efficient formal synthesis of SCH 351448, a compound that activates the low-density lipoprotein receptor (LDL-R) and has potential for treating hypercholesterolemia. The study utilizes a combination of tandem cross-metathesis (CM)/oxa-Michael reaction, 1,4-syn aldol reaction, tandem oxidation/oxa-Michael reaction, and Suzuki coupling reaction to synthesize the target compound. Key chemicals involved include hydroxy alkene 10, (E)-crotonaldehyde, tetrahydropyran aldehyde 8, ketone 9, epoxide 6, dithiane 7, and alkyne 4. The researchers successfully demonstrated the utility of these tandem reactions under mild conditions, achieving high yields and stereoselectivity. The study concludes that the convergent synthetic route is effective and could be broadly applicable for synthesizing analogues of SCH 351448 for further biological studies.