Chiral version of the Burgess reagent and its reactions with oxiranes: application to the formal enantiodivergent synthesis of balanol.
An efficient formal synthesis of a (-)-balanol intermediate ( 25a) from cyclohexadiene oxide was accomplished in eight steps. An asymmetric version of the Burgess reagent allows for an enantiodivergent approach to both enantiomers of balanol from a racemic starting material.
Sullivan
Bradford
B
Department of Chemistry, Brock University, Ontario, Canada.
Gilmet
Jacqueline
J
Leisch
Hannes
H
Hudlicky
Tomas
T
D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry; D053138:Cyclohexenes / Q000737:chemistry*; D005027:Ethylene Oxide / Q000737:chemistry*; D062385:Hydroxybenzoates / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D001381:Azepines; D053138:Cyclohexenes; D062385:Hydroxybenzoates; D007202:Indicators and Reagents; C048401:1,4-cyclohexadiene; C015405:ophiocordin; D005027:Ethylene Oxide