Title: Microwave-assisted traceless synthesis of hydantion-fused beta-carboline scaffold
Authors: Yeh, Wen-Pin
Chang, Wong-Jin
Sun, Mei-Lian
Sun, Chung-Ming
Department of Applied Chemistry
Issue Date: 26-Nov-2007
Abstract: Multistep microwave-assisted reactions toward the synthesis of hydantoin-fused tricyclic tetrahydro-beta-carbolines on the soluble polymer support have been developed. Polymer-bound tryptophan with various aldehydes has been subjected to Pictet-Spengler reaction to obtain tricyclic beta-carboline conjugates. The terminal hydantoinyl moiety is constructed across polymer-bound beta-carbolines by the reaction with various isocyanates under microwave irradiation to form urea intermediate. Simultaneous intramolecular cyclization of urea followed by cleavage of the polymer support leads to a traceless synthesis of tetracyclic scaffolds in high yield and high purity. (c) 2007 Elsevier Ltd. All rights reserved.
URI: http://dx.doi.org/10.1016/j.tet.2007.09.054
ISSN: 0040-4020
DOI: 10.1016/j.tet.2007.09.054
Volume: 63
Issue: 48
Begin Page: 11809
End Page: 11816
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