Synthesis of the fused polyether core of hemibrevetoxin B by two-directional ring-closing metathesis.
The tetracyclic fused polyether core of the marine natural product hemibrevetoxin B has been prepared in an efficient manner by using a strategy in which ring-closing metathesis (RCM) reactions were employed for ring synthesis. Simultaneous construction of the A and D rings was accomplished by double two-directional RCM of a tetraene. [reaction: see text]
Clark
J Stephen
JS
WestCHEM, Department of Chemistry, Joseph Black Building, University of Glasgow, University Avenue, Glasgow G12 8QQ, United Kingdom. stephenc@chem.gla.ac.uk
Grainger
Damian M
DM
Ehkirch
Alexandra A-C
AA
Blake
Alexander J
AJ
Wilson
Claire
C
D003500:Cyclization; D004987:Ethers / Q000737:chemistry*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D008387:Marine Toxins / Q000138:chemical synthesis*; D008956:Models, Chemical
D004987:Ethers; D006576:Heterocyclic Compounds, 4 or More Rings; D008387:Marine Toxins; C409729:hemibrevetoxin B