Electrocyclization??Mediated Approach to 2??Methyltriclisine, an Unnatural Analog of the Azafluoranthene Alkaloid Triclisine

…, ABJ Bracca, F Rinaldi, TS Kaufman

Index: Silveira, Claudio C.; Larghi, Enrique L.; Mendes, Samuel R.; Bracca, Andrea B. J.; Rinaldi, Francieli; Kaufman, Teodoro S. European Journal of Organic Chemistry, 2009 , # 27 p. 4637 - 4645

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Citation Number: 9

Abstract

Abstract The synthesis of 2-methyltriclisine, an unnatural analog of the azafluoranthene alkaloid triclisine, is reported. The synthesis was achieved in 10 steps and 21% overall yield from 2-bromo-3, 4-dimethoxybenzaldehyde, through the intermediacy of 3, 4- dimethoxyfluoren-9-one. Construction of the heterocyclic ring entailed the para-Claisen rearrangement of an allyl-4-fluorenyl ether, followed by isomerization of the resulting 2- ...