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DOI: 10.1055/s-2006-947335
Biomimetic Synthesis of trans,syn,trans-Fused Polycyclic Ethers
Publikationsverlauf
Received
24 February 2006
Publikationsdatum:
24. Juli 2006 (online)


Abstract
This account describes potentially biomimetic tandem regio- and stereoselective oxacyclizations of acyclic polyepoxide substrates to provide trans,syn,trans-fused polycyclic ether structures, as found in marine natural products exemplified by brevetoxins, ciguatoxins, and maitotoxin.
1 Introduction: Occurrence and Biological Activity of Fused Polycyclic Ether Natural Products
2 Biosynthetic Origins of Fused Polycyclic Ether Natural Products
3 Initial Studies Directed towards Tandem endo-Regioselective Cyclizations to Fused Polycyclic Ether Structures
4 Conversion of Terpene-Derived Polyepoxides to trans,syn,trans-Fused Polyoxepanes
5 Synthesis of trans,syn,trans-Polypyran from 1,4,7-Triepoxide
6 Substituent Effects on endo-Regioselective Polycyclizations
7 Future Directions for Exploration and Discovery
Key words
biomimetic synthesis - fused polycyclic ethers - polyepoxides - regioselectivity - stereoselectivity