88308-87-6Relevant academic research and scientific papers
Highly diastereoselective esterification of ketenes generated in situ from acyl chlorides with (R)-pantolactone derivatives
Yamagami, Takafumi,Hatsuda, Masanori,Utsugi, Masayuki,Kobayashi, Ryo,Moritani, Yasunori
supporting information, p. 7467 - 7470 (2013/12/04)
Our mechanistic investigations have revealed that Et3N is a key requirement for the highly diastereoselective formation of esters from the corresponding acyl chlorides with (R)-pantolactone via ketene-derived complexes. Furthermore, we have discovered that (R)-N-benzyl-pantolactam is a more effective chiral alcohol than (R)-pantolactone for the esterification of in situ generated ketenes. Ketene esterification with (R)-pantolactone derivatives is a powerful synthetic method for the synthesis of chiral α-arylpropionic acids. Our mechanistic investigations have revealed that Et3N is a key requirement for the predominant formation of ketenes from acyl chlorides, and (R)-N-benzylpantolactam was a much more effective chiral auxiliary.
Rational design of a topical androgen receptor antagonist for the suppression of sebum production with properties suitable for follicular delivery
Mitchell, Lorna H.,Johnson, Theodore R.,Lu, Guang Wei,Du, Daniel,Datta, Kaushik,Grzemski, Felicity,Shanmugasundaram, Veerabahu,Spence, Julie,Wade, Kim,Wang, Zhi,Sun, Kevin,Lin, Kristin,Hu, Lain-Yen,Sexton, Karen,Raheja, Neil,Kostlan, Catherine,Pocalyko, David
supporting information; experimental part, p. 4422 - 4427 (2010/09/04)
A novel nonsteroidal androgen receptor antagonist, (R)-4-(1-benzyl-4,4- dimethyl-2-oxopyrrolidin-3-yloxy)-2-(trifluoromethyl)benzonitrile (1), for the topical control of sebum production is reported. This compound, which is potent, selective, and efficacious in the clinically validated golden Syrian hamster ear animal model, was designed to be delivered to the pilosebaceous unit, the site of action, preferentially by the follicular route.
