192057-38-8Relevant academic research and scientific papers
Total synthesis of (+)-brasilenyne. Application of an intramolecular silicon-assisted cross-coupling reaction
Denmark, Scott E.,Yang, Shyh-Ming
, p. 12432 - 12440 (2004)
The first enantioselective total synthesis of (+)-brasilenyne (1) has been achieved in 19 linear steps, with 5.1% overall yield from L-(S)-malic acid. The construction of the oxonin core containing a 1,3-cis, cis diene unit was accomplished with a tandem ring-closing metathesis/silicon-assisted intramolecular cross-coupling reaction. In addition, a key propargylic stereogenic center was created through a novel, highly diastereoselective ring opening of a 1,3-dioxolanone promoted by TiCl4. This reaction proceeded through an oxocarbenium ion intermediate and the asymmetric induction was fully controlled by L-malic acid residue. The C(8) stereogenic center was set by a reagent-controlled asymmetric allylboration.
Novel glucocorticoid antedrugs possessing a 21-(γ-lactone) ring
Angell, Richard M.,Biggadike, Keith,Farrell, Rosanne M.,Flack, Stephen S.,Hancock, Ashley P.,Irving, Wendy R.,Lynn, Sean M.,Procopiou, Panayiotis A.
, p. 831 - 839 (2007/10/03)
Pregnane derivatives bearing γ-butyrolactones at C21 were prepared and tested as glucocorticoid agonists. The compounds were also tested for their liability in human plasmas. The compounds were found to be rapidly hydrolyzed by the enzyme paraoxonase to the respective hydroxyacids.
