13395-73-8Relevant articles and documents
Total Syntheses of Pyocyanin, Lavanducyanin, and Marinocyanins A and B
Kohatsu, Haruki,Kamo, Shogo,Tomoshige, Shusuke,Kuramochi, Kouji
supporting information, p. 7311 - 7314 (2019/10/02)
Total syntheses of pyocyanin, lavanducyanin, and marinocyanins A and B have been accomplished. The N-substituted phenazin-1-one skeleton, a common framework of these natural products, was constructed through the oxidative condensation of pyrogallol with N-substituted benzene-1,2-diamine under an oxygen atmosphere in a single step. Regioselective bromination with N-bromosuccinimide at the C-2 position of N-alkylated phenazin-1-ones afforded brominated natural products.
Manganese(III) acetate based oxidation of substituted α′-position on cyclic α,β-unsaturated ketones
Tanyeli, Cihangir,Iyigün, ?igdem
, p. 7135 - 7139 (2007/10/03)
Selective oxidation of the tertiary α′-position on various 2-cyclopentenone, 2-cyclohexenone and aromatic ketone derivatives with manganese(III) acetate is described.
A novel extension of the Stork-Jung vinylsilane Robinson annelation procedure for the introduction of the cyclohexene of guanacastepene
Snider, Barry B,Shi, Bo
, p. 9123 - 9126 (2007/10/03)
A new annelation procedure has been developed in a model system to introduce the cyclohexene ring of guanacastepene. Cyclohexenone 16 is prepared by sequential methylation and alkylation with allylic iodide 15. One-pot epoxidation, protodesilylation and hydrolysis of the THP forms dione 19, which cyclizes with NaOMe to 24 in 57% overall yield. Reduction, Mitsunobu inversion, and selective oxidation of the primary alcohol forms model 29. Phenyldimethylsilyl allylic iodide 36 is easier to make and more stable than trimethylsilyl allylic iodide 6 used by Stork.
