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Synlett 2012; 23(13): 1882-1892
DOI: 10.1055/s-0031-1290692
DOI: 10.1055/s-0031-1290692
account
Total Synthesis of (±)-Dragmacidin E; Problems Solved and Lessons Learned
Further Information
Publication History
Received: 02 April 2012
Accepted after revision: 30 April 2012
Publication Date:
16 July 2012 (online)
Abstract
(±)-Dragmacidin E was synthesized in 25 steps from commercially available 7-(benzyloxy)indole. Key transformations in the preparation of this sponge metabolite include (a) a Witkop cyclization to establish the bridging indole core, (b) cyclo-dehydrative pyrazinone formation to unite the two indole-bearing components, and (c) late-stage guanidine installation through chemoselective carbonyl activation.
1 Introduction
2 Results and Discussion
2.1 Model System Synthesis
2.2 (±)-Dragmacidin E Synthesis
3 Conclusions
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