ETH Zürich HCI H335, Wolfgang-Pauli-Strasse 10, 8093 Zürich, Switzerland.
Chemistry. 2012 Mar 19;18(12):3598-610. doi: 10.1002/chem.201102797. Epub 2012 Feb 16.
A convergent synthesis of bafilomycin A(1), a potent inhibitor of V-type ATPases, is presented. The synthesis relies on the zinc triflate mediated diastereoselective addition of a complex enyne to a sensitive aldehyde as the key fragment coupling. A ruthenium-catalyzed trans-reduction of the resulting propargylic enyne efficiently installs the required C10-C13 trans,trans-diene subunit, implementing an alternative strategy to traditional palladium-catalyzed cross-coupling strategies. A highly selective oxidation of a secondary hydroxyl group in a triol sets the stage for the completion of the synthesis.
呈现了一种巴弗洛霉素 A(1)的收敛性合成方法，巴弗洛霉素 A(1)是一种 V 型 ATP 酶的有效抑制剂。该合成方法依赖于三氟甲磺酸锌介导的立体选择性加成反应，其中一个复杂的烯炔与一个敏感的醛作为关键片段偶联。通过钌催化的反式还原反应，有效地在所得的炔丙基烯炔上安装了所需的 C10-C13 反式, 反式-二烯亚基，实现了一种替代传统钯催化交叉偶联策略的策略。在三醇中选择性地氧化一个仲羟基基团为合成的完成奠定了基础。
