Total synthesis of (±)-dragmacidin E; Problems solved and lessons learned

Ken S. Feldman, Paiboon Ngernmeesri

Research output: Contribution to journalArticle

15 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)1882-1892
Number of pages11
JournalSynlett
Volume23
Issue number13
DOIs
StatePublished - Jul 23 2012

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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