Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany.
Nat Chem. 2009 Jun;1(3):225-8. doi: 10.1038/nchem.215. Epub 2009 May 22.
Cascade reactions enable the rapid build-up of molecular complexity from relatively simple starting materials. Both rapid construction and the ability to prepare related structures are crucial to the study of biological activities. Here, we report an efficient, highly enantioselective and diastereoselective total synthesis of ricciocarpin A. The key feature of the synthesis is a one-pot, three-step, organocatalytic reductive Michael-Tishchenko cascade. The conciseness and flexibility of this approach not only resulted in the synthesis of the natural product, but also of its antipode and four other structural analogues. A preliminary biological evaluation of these compounds identified an analogue with significantly improved molluscicidal activity.
级联反应能够使分子复杂性从相对简单的起始原料中快速构建。快速构建和制备相关结构的能力对于研究生物活性至关重要。在这里，我们报告了一种高效、高对映选择性和非对映选择性的 Ricciocarpin A 的全合成方法。该合成的关键特征是一锅三步有机催化还原迈克尔-Tishchenko 级联反应。这种方法的简洁性和灵活性不仅导致了天然产物的合成，还导致了其对映异构体和其他四个结构类似物的合成。对这些化合物的初步生物学评价表明，一种类似物具有显著改善的杀软体动物活性。
