1432583-86-2Relevant articles and documents
Directed metalation?£?cross-coupling strategies. Total syntheses of the alleged and the revised phenanthrene natural product gymnopusin
Wang, Xin,Fu, Jian-Min,Snieckus, Victor
, p. 2680 - 2694 (2013/03/13)
The total synthesis of gymnopusin (2) is described. The originally assigned structure for gymnopusin 1a was found to be incorrect by total synthesis using the Directed ortho-Metalation (DoM)?£?Cross- Coupling?£?Directed remote Metalation (DreM) sequence, a demonstrable key strategy for the regioselective construction of the 9-phenanthrol core. The revised structure of gymnopusin (2) was confirmed by synthesis by adopting the same strategy but involving a key remote anionic Fries-rearrangement step. Both routes highlight methodologies and concepts which may be of value in the regiocontrolled synthesis of phenanthrenoids specifically and in complex polycyclic aromatics in general. Copyright