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- Title
Directed MetalationCross-Coupling Strategies. Total Syntheses of the Alleged and the Revised Phenanthrene Natural Product Gymnopusin.
- Authors
Wang, Xin; Fu, Jian-min; Snieckus, Victor
- Abstract
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 (D oM)Cross-CouplingDirected 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.
- Subjects
METALATION; CHEMICAL synthesis; PHENANTHRENE; REGIOSELECTIVITY (Chemistry); POLYCYCLIC aromatic compounds
- Publication
Helvetica Chimica Acta, 2012, Vol 95, Issue 12, p2680
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.201200564