Epoxy allylic carbocations as conceptual intermediates in the biogenesis of diverse marine oxylipins.
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.
Gerwick
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College of Pharmacy, Oregon State University, Corvallis 97331, USA.
D000498:Allyl Compounds / Q000737:chemistry / Q000378:metabolism; D000818:Animals; D002412:Cations / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry / Q000378:metabolism; D004987:Ethers / Q000737:chemistry / Q000378:metabolism; D056890:Eukaryota / Q000378:metabolism*; D005231:Fatty Acids, Unsaturated / Q000737:chemistry / Q000378:metabolism; D005233:Fatty Alcohols / Q000737:chemistry / Q000378:metabolism; D007783:Lactones / Q000737:chemistry / Q000378:metabolism; D008055:Lipids / Q000096:biosynthesis* / Q000737:chemistry*; D015394:Molecular Structure; D011453:Prostaglandins / Q000737:chemistry / Q000378:metabolism
D000498:Allyl Compounds; D002412:Cations; D004852:Epoxy Compounds; D004987:Ethers; D005231:Fatty Acids, Unsaturated; D005233:Fatty Alcohols; D007783:Lactones; D008055:Lipids; D011453:Prostaglandins