Synthetic and mechanistic studies of the retro-Claisen rearrangement. 4. An application to the total synthesis of (+)-Laurenyne

Robert K Boeckman Jr; Jing Zhang; Michael R Reeder

doi:10.1021/ol0267174

Synthetic and mechanistic studies of the retro-Claisen rearrangement. 4. An application to the total synthesis of (+)-Laurenyne

Org Lett. 2002 Oct 31;4(22):3891-4. doi: 10.1021/ol0267174.

Authors

Robert K Boeckman Jr¹, Jing Zhang, Michael R Reeder

Affiliation

¹ Department of Chemistry, University of Rochester, Rochester, New York 14627-0216, USA. rkb@rkbmac.chem.rochester.edu

PMID: 12599485
DOI: 10.1021/ol0267174

Abstract

[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.

Publication types

Research Support, U.S. Gov't, P.H.S.

MeSH terms

Cyclization
Cyclobutanes / chemistry
Heterocyclic Compounds, 1-Ring / chemical synthesis*
Hydrocarbons, Chlorinated / chemical synthesis*
Stereoisomerism

Substances

Cyclobutanes
Heterocyclic Compounds, 1-Ring
Hydrocarbons, Chlorinated
laurenyne

Grants and funding

GM-30345/GM/NIGMS NIH HHS/United States