Chaubet Guilhem, Goh Shermin S, Mohammad Mujahid, Gockel Birgit, Cordonnier Marie-Caroline A, Baars Hannah, Phillips Andrew W, Anderson Edward A
Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, UK.
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.
Chemistry. 2017 Oct 9;23(56):14080-14089. doi: 10.1002/chem.201703229. Epub 2017 Sep 8.
Full details of the total synthesis of the Schisandraceae nortriterpenoid natural product rubriflordilactone A are reported. Palladium- and cobalt-catalyzed polycyclizations were employed as key strategies to construct the central pentasubstituted arene from bromoendiyne and triyne precursors. This required the independent assembly of two AB ring aldehydes for combination with a common diyne component. A number of model systems were explored to investigate these two methodologies, and also to establish routes for the installation of the challenging benzopyran and butenolide rings.
报道了五味子科东北三萜类天然产物红绵内酯A的全合成详细信息。钯催化和钴催化的多环化反应被用作关键策略,以从溴代双烯炔和三炔前体构建中心五取代芳烃。这需要独立组装两个AB环醛,以便与一个共同的双炔组分结合。探索了许多模型体系来研究这两种方法,同时也建立了引入具有挑战性的苯并吡喃环和丁烯内酯环的路线。