Synlett 2006(12): 1816-1828  
DOI: 10.1055/s-2006-947335
ACCOUNT
© Georg Thieme Verlag Stuttgart · New York

Biomimetic Synthesis of trans,syn,trans-Fused Polycyclic Ethers

Jason C. Valentine, Frank E. McDonald*
Department of Chemistry, Emory University, Atlanta, GA 30322, USA
Fax: +1(404)7276586; e-Mail: fmcdona@emory.edu;
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Publikationsverlauf

Received 24 February 2006
Publikationsdatum:
24. Juli 2006 (online)

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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