Protecting-Group-Free Synthesis of Chokols

作者:Perez Morales Carmen; Catalan Julieta; Domingo Victoriano; Gonzalez Delgado Jose A; Dobado Jose A; Mar Herrador M; Quilez del Moral Jose F; Barrero Alejandro F
来源:Journal of Organic Chemistry, 2011, 76(8): 2494-2501.
DOI:10.1021/jo102280n

摘要

As a result of a combined theoretical and experimental study, we describe a two-step protocol for the preparation of an optically pure, multifunctional, cyclopentanic core shared by a number of natural products. This process is based on a hitherto unreported Ti(III)-mediated diastereoselective cyclization in which the hydroxy-directed template effect played by the Ti(III) species was found to be crucial for the stereoselective outcome of the reaction. The viability of this concept was confirmed with the first protecting-group free synthesis of three enantiopure chokols, namely, chokols K, E, and B.

  • 出版日期2011-4-15