137639-65-7Relevant academic research and scientific papers
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
SYNTHETIC STRATEGIES BASED ON AROMATIC METALATION - CROSS COUPLING LINKS. REGIOSPECIFIC SYNTHESIS OF THE PHENANTHRENE NATURAL PRODUCT GYMNOPUSIN
Wang, X.,Snieckus, V.
, p. 4879 - 4882 (2007/10/02)
An efficient synthesis of gymnopusin (2) using ortho metalation, Suzuki cross coupling, and new anionic Fries rearrangement (3) steps has been achieved.
