Barrett Anthony G. M., Boys Mark L., Boehm Terri L.
Departments of Chemistry, Imperial College of Science, Technology and Medicine, London SW7 2AY, England, and Colorado State University, Fort Collins Colorado 80523.
J Org Chem. 1996 Jan 26;61(2):685-699. doi: 10.1021/jo951413z.
The total synthesis of (+)-papuamine, the antipode of the C(2)-symmetric, optically active, pentacyclic diamine natural product, starting from a chiral diol is described. The diol is available via an asymmetric Diels-Alder reaction between 1,3-butadiene and di-(-)-menthyl fumarate. The key transformation in the synthesis is an intramolecular Pd(0)-catalyzed (Stille) coupling reaction to form the central 13-membered diazadiene macrocyclic ring.
描述了从手性二醇出发全合成（+）-帕普胺，它是具有C（2）对称性、光学活性的五环二胺天然产物的对映体。该二醇可通过1,3-丁二烯与富马酸二（-）-薄荷酯之间的不对称狄尔斯-阿尔德反应得到。合成中的关键转化是分子内钯（0）催化的（施蒂勒）偶联反应，以形成中心的13元二氮二烯大环。
