TY - JOUR
T1 - Synthesis of α,β-unsaturated epoxy ketones utilizing a bifunctional sulfonium/phosphonium ylide
AU - Eskandari, Roozbeh
AU - Hess, Jeremy P.
AU - Tochtrop, Gregory P.
N1 - Funding Information:
Financial support was provided in part by the National Science Foundation (NSF-CHE) Award No. 1904530 and the Department of Defense (DOD-CDMRP) Award No. W81XWH-16-1-0699. We would also like to thank staff members from NMR core facility at Department of Chemistry at Case Western Reserve University for helpful advice with NMR experiments and Larry Sallans for high-resolution mass spectrometry measurements at R. Marshall Wilson Mass Spectrometry Facility at University of Cincinnati.
Publisher Copyright:
© The Royal Society of Chemistry 2021.
PY - 2021/7/25
Y1 - 2021/7/25
N2 - Herein, a new protocol for rapid synthesis of α,β-unsaturated epoxy ketones utilizing a bifunctional sulfonium/phosphonium ylide is described. This approach comprises two sequential chemoselective reactions between sulfonium and phosphonium ylides and two distinct aldehydes, which allows for the rapid construction of a variety of unsymmetric α,β-unsaturated epoxy ketones. This methodology allows the rapid construction of the core reactive functionality of a family of lipid peroxidation products, the epoxyketooctadecenoic acids, but can be further broadly utilized as a useful synthon for the synthesis of natural products, particularly those derived from oxidized fatty acids. Accordingly, a protocol utilizing this approach to synthesize the epoxyketooctadecenoic acid family of molecules is described.
AB - Herein, a new protocol for rapid synthesis of α,β-unsaturated epoxy ketones utilizing a bifunctional sulfonium/phosphonium ylide is described. This approach comprises two sequential chemoselective reactions between sulfonium and phosphonium ylides and two distinct aldehydes, which allows for the rapid construction of a variety of unsymmetric α,β-unsaturated epoxy ketones. This methodology allows the rapid construction of the core reactive functionality of a family of lipid peroxidation products, the epoxyketooctadecenoic acids, but can be further broadly utilized as a useful synthon for the synthesis of natural products, particularly those derived from oxidized fatty acids. Accordingly, a protocol utilizing this approach to synthesize the epoxyketooctadecenoic acid family of molecules is described.
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U2 - 10.1039/d1cc02475b
DO - 10.1039/d1cc02475b
M3 - Article
C2 - 34180477
AN - SCOPUS:85111063311
SN - 1359-7345
VL - 57
SP - 7136
EP - 7139
JO - Chemical Communications
JF - Chemical Communications
IS - 58
ER -