Please use this identifier to cite or link to this item: https://scholarbank.nus.edu.sg/handle/10635/116638
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. 
Ganesan, A. 
Issue Date: 18-Nov-1999
Citation: 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
URI: http://scholarbank.nus.edu.sg/handle/10635/116638
ISSN: 15237060
Appears in Collections:Staff Publications

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