Epoxy allylic carbocations as conceptual intermediates in the biogenesis of diverse marine oxylipins

Lipids
W H Gerwick

Abstract

Marine organisms, especially marine algae, are extremely rich in a diversity of novel oxylipin structures. Many of these oxylipins contain functionalities and rings of a type and location unknown in mammalian systems. In this perspective reviewing marine oxylipins, a proposal is formulated for the central intermediacy of an epoxy allylic carbocation in the biogenesis of these diverse structures. This proposal is strengthened by the relatively large number of examples which are consistent with this type of mechanistic transformation.

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Citations

Apr 21, 1999·Progress in Lipid Research·A Grechkin
Sep 12, 2002·Annual Review of Plant Biology·Ivo Feussner, Claus Wasternack
Nov 21, 2007·Proceedings of the National Academy of Sciences of the United States of America·Claus SchneiderAlan R Brash
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Feb 3, 2000·Phytochemistry·Z D JiangW H Gerwick
Oct 14, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Simen G AntonsenJens M J Nolsøe
Nov 17, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jens M J NolsøeTrond V Hansen
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Nov 2, 2018·The Journal of Organic Chemistry·Jens M J NolsøeYngve H Stenstrøm
Aug 28, 2021·Biochimica Et Biophysica Acta. Molecular and Cell Biology of Lipids·Alexander N GrechkinYana Y Toporkova

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