The sporolide quinone acid is a key fragment in the biosynthesis of the complex heptacyclic marine metabolite sporolide. We report a concise enantioselective route to this fragment, which is obtained in seven steps with 65% overall yield from trimethoxybenzene. The enantioselective transfer reduction is achieved by Ipc2BCl, and the absolute configuration of the product secured by X-ray analysis of its cinchonine salt. The target fragment is then obtained by methylation and oxidation to the quinone by AgO.
Pascal Turberg, Charlotte Grossiord, Hervé Cochard, Laura Mekarni
Marcos Rubinstein, Antonio Sunjerga, Farhad Rachidi-Haeri, Thomas Chaumont
Sandor Kasas, María Inés Villalba