Fachbereich Chemie and Konstanz Research School Chemical Biology, Universität Konstanz, Universitätsstrasse 10, Postfach 720, 78457 Konstanz, Germany.
Chemistry. 2010 Aug 2;16(29):8805-21. doi: 10.1002/chem.201000804.
A cobalt(I)-mediated convergent and asymmetric total synthesis of angucyclinones with an aromatic B ring has been developed. In the course of our research, we synthesized three naturally occurring anguclinone derivatives, namely, (+)-rubiginone B(2) (1), (-)-8-O-methyltetrangomycin (2), and (-)-tetrangomycin (3). By combining 3-hydroxybenzoic acid, 3-methoxybenzoic acid, citronellal, and geraniol as starting materials in a convergent way, we were able to synthesize chiral triyne chains, which were cyclized with [CpCo(C(2)H(4))(2)] (Cp=cyclopentadienyl) by means of an intramolecular [2+2+2] cycloaddition to their corresponding tetrahydrobenzo[a]anthracenes. Successive oxidation and deprotection steps led to the above-mentioned natural products 1-3.
已开发出钴（I）介导的蒽环酮的会聚和不对称全合成方法，其中苯环具有芳香性。在我们的研究过程中，我们合成了三种天然存在的蒽环酮衍生物，即（+）-rubiginone B（2）（1）、（-）-8-O-甲基四放线菌素（2）和（-）-四放线菌素（3）。通过将 3-羟基苯甲酸、3-甲氧基苯甲酸、橙花醛和香叶醇作为起始原料进行会聚合成，我们能够合成手性三炔链，然后通过分子内[2+2+2]环加成将其与[CpCo（C（2）H（4））（2）]（Cp=环戊二烯基）环化，得到相应的四氢苯并[a]蒽。随后的氧化和脱保护步骤导致了上述天然产物 1-3 的生成。
