Studies on the synthesis of gymnodimine. Stereocontrolled construction of the tetrahydrofuran subunit.
[reaction: see text]. A bis-(2,6-dichlorobenzyl) ether is shown to undergo efficient and highly stereoselective intramolecular iodoetherification to yield a cis-2,5-disubstituted tetrahydrofuran, thus providing a powerful illustration of a stereodirecting effect first noted by Rychnovsky and Bartlett. The tetrahydrofuran was transformed into a subunit suitable for incorporation into the shellfish toxin gymnodimine.
White
James D
JD
Department of Chemistry, Oregon State University, Corvallis, Oregon 97331-4003, USA. james.white@orst.edu
Wang
Guoqiang
G
Quaranta
Laura
L
D018360:Crystallography, X-Ray; D003500:Cyclization; D005663:Furans / Q000737:chemistry*; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis*; D006844:Hydrocarbons, Cyclic / Q000138:chemical synthesis*; D007097:Imines / Q000138:chemical synthesis*; D007455:Iodine / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
D005663:Furans; D006575:Heterocyclic Compounds, 3-Ring; D006844:Hydrocarbons, Cyclic; D007097:Imines; C018674:tetrahydrofuran; C407350:gymnodimine; D007455:Iodine