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Epoxy allylic carbocations as conceptual intermediates in the biogenesis of diverse marine oxylipins
Author(s) -
Gerwick William H.
Publication year - 1996
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02587906
Subject(s) - biogenesis , carbocation , allylic rearrangement , oxylipin , diterpene , algae , chemistry , lipidology , biology , botany , stereochemistry , clinical chemistry , biochemistry , organic chemistry , catalysis , enzyme , gene
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.