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Extra info for Advanced Problems in Organic Reaction Mechanisms
O A H - I H 1 2 H H (+)-Hirsutene 55. A 1 , 3 - C y d o p e n t a n e d i o n e to 1 , 4 - C y c l o h e x a n e d i o n e Transformation 2,2-Dialkylated 1,3-cyclopentanediones undergo facile 13-dicarbonyl cleavage on treatment with aqueous alkali, and this process constitutes an excellent synthesis of 5-substituted 4-oxoalkanoic acids. The conversion of 1 into 2 was presumed to proceed in this way for more than 10 years. Closer examination of this transformation, however, revealed the situation to be more complex.
Compounds 2 and 4 showed a much more pronounced growth-stimulating effect than PQQ, while 3 also showed "a marked effect". Give mechanisms for the reaction of 1 with L-tryptophan to produce 2, 3 and 4. co~ HO2c ~ "N" "if" "O O HO2 ~-~N C02H C02H -o HO2C~ " I ~ L " ~ H2C~ H H 3 4 N "O 37 Advanced Problems in Organic Reaction Mechanisms 66. An Unexpected Result from an Attempted Double Bischler-Napieralski Reaction As part of a programme designed to produce compounds with axial chirality, double B ischlerNapieralski reactions were carried out with oxamide derivatives of c0-arylalkylamines.
An Efficient Chromene Synthesis Lithiation of commercially available phenyl vinyl sulfoxide with LDA followed by reaction with sodium 2-acetyl-4-methylphenoxide gave the expected alcohol in 90% yield. This was not very stable but was nevertheless heated under reflux in ethanolic sodium ethoxide (excess) for 19 hours. Standard work-up and purification gave the chromene 1, also in 90% yield. Give a mechanism for the formation of 1.