Traceless Release of Alcohols Using Thiol-Sensitive Oxanorbornadiene Linkers

Organic Letters
Allison G AioubM G Finn

Abstract

A class of ester-amide oxanorbornadiene (EA-OND) molecules was developed to release alcohol cargos by succinimide formation upon addition of a thiol reagent. The resulting ring-closed adducts undergo further fragmentation by retro-Diels-Alder reaction to release a furan moiety in a manner similar to oxanorbornadiene diesters. The rates of each of these fragmentation pathways in the same medium were found to be sensitive to the steric nature of the amide substituent. Alcohol release was much faster in protic solvents than in aprotic ones, suggesting that this system may be useful for rapid response to thiols in biological environments. Accordingly, the attachment and thiol-dependent release of cholesterol was characterized as an example of the manipulation of a drug-like cargo.

References

Aug 29, 2003·Cellular and Molecular Life Sciences : CMLS·K J Reissner, D W Aswad
Feb 29, 2008·Bioorganic & Medicinal Chemistry·Luca BanfiRenata Riva
Jul 23, 2009·Journal of the American Chemical Society·Vu HongM G Finn
Mar 30, 2012·Journal of the American Chemical Society·Alexander A KislukhinM G Finn
Jan 13, 2015·Journal of Controlled Release : Official Journal of the Controlled Release Society·Qing PanJustin Hanes
Nov 1, 2017·Journal of the American Chemical Society·Richard Stevenson, Guillaume De Bo

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