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|Title:||The N-acyliminium Pictet-Spengler condensation as a multicomponent combinatorial reaction on solid phase and its application to the synthesis of demethoxyfumitremorgin C analogues|
|Authors:||Wang, H. |
|Source:||Wang, H.,Ganesan, A. (1999-11-18). The N-acyliminium Pictet-Spengler condensation as a multicomponent combinatorial reaction on solid phase and its application to the synthesis of demethoxyfumitremorgin C analogues. Organic Letters 1 (10) : 1647-1649. ScholarBank@NUS Repository.|
|Abstract:||(matrix presented). L-Tryptophan immobilized on polystyrene-Wang resin was sequentially reacted with an aldehyde and Fmoc-amino acid chloride. This generates a transient N-acyliminium species which undergoes Pictet-Spengler condensation to give a mixture of cis and trans tetrahydro-β-carbolines. Removal of the Fmoc protecting group, with concomitant diketopiperazine formation, results in cyclative cleavage of the desired products from the resin.|
|Source Title:||Organic Letters|
|Appears in Collections:||Staff Publications|
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