65529-50-2Relevant academic research and scientific papers
Jatrophane diterpenes: Preparation of the western fragment of pl-3
Lentsch, Christoph,Fuerst, Rita,Mulzer, Johann,Rinner, Uwe
, p. 919 - 923 (2014/03/21)
Jatrophane diterpenes are structurally intriguing natural products with promising biological properties. Herein, the synthesis of the western fragment of the Euphorbiaceae constituent Pl-3 starting from (1R,5S)-bicyclo[3.2.0]hept- 2-en-6-one is described. Key steps in the sequence include a Baeyer-Villiger oxidation, an iodolactonization reaction, and the installation of the northern side chain through the addition of a lithiated vinyl bromide. The overall efficiency of the route is increased by taking advantage of latent symmetry. The synthesis of the western fragment of Pl-3 is developed by taking advantage of the latent symmetry in an intermediate; both enantiomers are thus converted into the desired substrate. Key steps of the synthesis include a Baeyer-Villiger oxidation, an iodolactonization reaction, and the addition of a vinyllithium species to the completed cyclopentane moiety of the natural product.
A SIMPLE ENANTIOCOMPLEMENTARY ROUTE TO PROSTANOIDS; INVERSION OF CHIRALITY OF 2,5-DIHYDROXY-CYCLOPENT-3-ENYL-ACETIC ACID LACTONE DERIVATIVES
Toemoeskoezi, I.,Gruber, L.,Gulacsi, E.
, p. 3141 - 3144 (2007/10/02)
An enantiocomplementary route to PGA2 and PGE2 synthons is presented.
A SIMPLE ENANTIOSELECTIVE INVERSION IN CHIRAL 2-OXABICYCLOOCTA-6-EN-3-ONE, A KEY INTERMEDIATE FOR CHIRAL PROSTAGLANDIN SYNTHESES
Ishizuka, Naoyasu,Miyamura, Souji,Takeuchi, Tadashi,Achiwa, Kazuo
, p. 1123 - 1124 (2007/10/02)
A simple and effective inversion of (1R,5S)-2-oxabicycloocta-6-en-3-one into its enantiomer was described.
