38237-36-4Relevant academic research and scientific papers
Control of the regio- and diastereoselectivity for the preparation of highly functionalized terpenic cyclopentanes through radical cyclization
Arteaga, Jesus F.,Dieguez, Horacio R.,Gonzalez-Delgado, Jose A.,Quilez Del Moral, Jose F.,Barrero, Alejandro F.
supporting information; experimental part, p. 5002 - 5011 (2011/11/06)
The titanocene-mediated cyclization of suitably functionalized acyclic C10 epoxy-polyprenes leads, with moderate stereoselectivity, to high yields of functionalized terpenic cyclopentanes with three contiguous stereogenic centers. These highly functionalized cyclopentanes are useful intermediates for the synthesis of several natural compounds that include this interesting subunit in their structure. Both the regioselectivity of the process leading to cyclopentanes and the stereoselectivity of the cyclization could be controlled by using malonyl derivatives or α,β-unsaturated nitriles as radical acceptors. The titanocene-mediated cyclization of suitably functionalized acyclic C10 epoxy-polyprenes proceeds with acceptable stereochemical control and excellent yields. The process takes place through 5-exo-trig ring closures and gives cyclopentanes with three contiguous stereogenic centers with peripheral functional groups that are suitable for constructing structurally complex natural products. Copyright
