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Synthesis of Polycyclic Ethers by Two‐Directional Double Ring‐Closing Metathesis
Author(s) -
Clark J. Stephen,
Hamelin Olivier
Publication year - 2000
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(20000117)39:2<372::aid-anie372>3.0.co;2-y
Subject(s) - ring closing metathesis , chemistry , metathesis , allylic rearrangement , enol ether , enol , stereochemistry , ring (chemistry) , salt metathesis reaction , ether , allylic alcohol , ciguatoxin , organic chemistry , catalysis , polymerization , polymer , fishery , fish <actinopterygii> , biology
trans ‐Fused tricyclic ethers containing combinations of six‐, seven‐, eight‐, and nine‐membered rings are constructed using two‐directional double ring‐closing metathesis reactions (see scheme). Such double cyclizations of precursors bearing alkenes, allylic ethers, enol ethers, or alkynyl ethers offer a new strategy for the synthesis of brevetoxins and ciguatoxins. PMB=( p ‐MeOC 6 H 4 CH 2 ).