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Harnessing the Intrinsic Reactivity within the Aplysinopsin Series for the Synthesis of Intricate Dimers: Natural from Start to Finish

Harnessing the Intrinsic Reactivity within the Aplysinopsin Series for the Synthesis of Intricate Dimers: Natural from Start to Finish

Authors :
Adam Skiredj
Laurent Evanno
Mehdi A. Beniddir
Delphine Joseph
Guillaume Bernadat
Erwan Poupon
Source :
Synthesis. 47:2367-2376
Publication Year :
2015
Publisher :
Georg Thieme Verlag KG, 2015.

Abstract

Aplysinopsin monomers are considered as plausible biosynthetic precursors of the wider aplysinopsin family of marine alkaloids. The idea of harnessing their intrinsic reactivity to undertake the synthesis of dictazoles or cycloaplysinopsins logically emerged from this status. These biosynthetic considerations led us to the first total syntheses of dictazole B and other valuable cyclobutanes. When further exploiting pre-encoded reactivity, our first total synthesis of tubastrindole B originated from the ring-expansion cascade of its dictazole-type precursor. Moreover, the isolation of a transient biosynthetic intermediate combined with dimerization outcomes of a hydantoin-containing monomer allowed us to explain the formation of cycloaplysinopsins A and B. 1 Introduction 2 Easy Access to Dictazole Cyclobutanes 3 Synthesis of Cycloaplysinopsins by Ring Expansion 4 Conclusion and Future Prospects

Details

ISSN :
1437210X and 00397881
Volume :
47
Database :
OpenAIRE
Journal :
Synthesis
Accession number :
edsair.doi...........2890e07861b69d7ecd2173fce5f40b32
Full Text :
https://doi.org/10.1055/s-0034-1381032