Synthetic and mechanistic studies of the retro-Claisen rearrangement. 4. An application to the total synthesis of (+)-Laurenyne.
[formula: see text] A novel asymmetric total synthesis of marine natural product (+)-Laurenyne has been achieved. The key elements of the strategy are the sequential metal ion-templated SN2' cyclization affording a highly functionalized chiral vinyl cyclobutane and a retro-Claisen rearrangement for the construction of an eight-membered ring ether.
Boeckman
Robert K
RK
Department of Chemistry, University of Rochester, Rochester, New York 14627-0216, USA. rkb@rkbmac.chem.rochester.edu
Zhang
Jing
J
Reeder
Michael R
MR
D003500:Cyclization; D003503:Cyclobutanes / Q000737:chemistry; D006573:Heterocyclic Compounds, 1-Ring / Q000138:chemical synthesis*; D006843:Hydrocarbons, Chlorinated / Q000138:chemical synthesis*; D013237:Stereoisomerism
D003503:Cyclobutanes; D006573:Heterocyclic Compounds, 1-Ring; D006843:Hydrocarbons, Chlorinated; C455739:laurenyne