Substrate encapsulation: an efficient strategy for the RCM synthesis of unsaturated epsilon-lactones. Academic Article

abstract

• A facile substrate-encapsulated RCM-based synthesis of 7-membered lactones is reported. Coordination of the alpha,omega-dienyl ester precursor to the bulky Lewis acid (LA) aluminum tris(2,6-diphenylphenoxide) (ATPH) provides a protective extended steric pocket to the olefin moieties, thereby favoring intramolecular RCM over intermolecular ADMET oligomerization. The LA-encapsulated esters undergo ring-closure in the presence of Ru-based olefin metathesis catalysts to give previously difficult-to-access 7-membered beta,gamma- and gamma,delta-unsaturated lactones in good yields.

authors

• Pentzer, Emily

published proceedings

• Org Lett

altmetric score

• 3

author list (cited authors)

• Pentzer, E. B., Gadzikwa, T., & Nguyen, S. T.

citation count

• 22

complete list of authors

• Pentzer, Emily B||Gadzikwa, Tendai||Nguyen, SonBinh T

publication date

• December 2008

publisher

• American Chemical Society (ACS)  Publisher

published in

• Organic Letters  Journal

keywords

• Furans
• Lactones
• Ruthenium

PubMed Central ID

• 19053741

Digital Object Identifier (DOI)

• 10.1021/ol8022227

start page

• 5613

end page

• 5615

volume

• 10

issue

• 24

URL

• http://dx.doi.org/10.1021/ol8022227