1046471-27-5Relevant 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.
Toward the synthesis of didemnaketal B: A convergent synthesis of the C9-C28 subunit
Ito, Hisanaka,Inoue, Takaya,Iguchi, Kazuo
supporting information; experimental part, p. 3873 - 3876 (2009/07/09)
(Chemical Equation Presented) Synthesis of the C9-C28 subunit of didemnaketal B has been developed. This subunit was convergently prepared from four chiral synthons and at the longest linear sequence required 16 steps.
