Total Synthesis of (±)-Dragmacidin E; Problems Solved and Lessons Learned

Ken S. Feldman; Paiboon Ngernmeesri

doi:10.1055/s-0031-1290692

Synlett, Table of Contents

Synlett 2012; 23(13): 1882-1892
DOI: 10.1055/s-0031-1290692

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Total Synthesis of (±)-Dragmacidin E; Problems Solved and Lessons Learned

Ken S. Feldman*

^aChemistry Department, The Pennsylvania State University, University Park, PA 16802, USA

,

Paiboon Ngernmeesri

^bChemistry Department, Kasetsart University, Bangkok 10900, Thailand , Email: ksf@chem.psu.edu

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Abstract

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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

Key words

total synthesis - alkaloids - marine natural products - Witkop cyclization - pyrazinone

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References

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