Total syntheses of multicaulins via oxidative photocyclization of stilbenes.
@article{Secinti2014TotalSO, title={Total syntheses of multicaulins via oxidative photocyclization of stilbenes.}, author={Hatice Secinti and Serdar Burmaoglu and Ramazan Altundas and Hasan SeÇen}, journal={Journal of natural products}, year={2014}, volume={77 9}, pages={ 2134-7 } }
The Wittig reaction of 3-isopropyl-4-methoxybenzaldehyde and 2,3-dimethylbenzylphosphonium bromide afforded the corresponding stilbene mixture 16. Oxidative photocyclization of stilbene 16 with iodine facilitated the first total synthesis of 7-isopropyl-6-methoxy-1,2-dimethylphenanthrene, multicaulin (1). The O-demethylation of 1 with BBr3 afforded the 7-isopropyl-1,2-dimethylphenanthren-6-ol, O-demethylmulticaulin (2).
5 Citations
Total synthesis of ent-(+)-cinanthrenol A
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This synthesis features a photo-promoted oxidative 6π-electron electrocyclization/aromatization for construction of the cyclopenta[a]phenanthren-17-one and Furukawa hydroxyl-directed cyclopropanation for the rare spiro[2,4]heptane.
Syntheses and evaluation of multicaulin and miltirone-like compounds as antituberculosis agents
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Four multicaulin and miltirone-like phenanthrene derivatives were synthesised and evaluated as antituber tuberculosis agents and the best antituberculosis activity was exhibited by 2-isopropylphenanthrene-3-ol.
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