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Frontispiece: Germacrene A–A Central Intermediate in Sesquiterpene Biosynthesis
Author(s) -
Xu Houchao,
Dickschat Jeroen S.
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202087262
Subject(s) - sesquiterpene , lability , germacrene , biosynthesis , germacrene d , reactivity (psychology) , ring (chemistry) , chemistry , stereochemistry , organic chemistry , medicine , enzyme , alternative medicine , pathology , chemical composition
Germacrene A shows a unique and interesting chemistry mainly characterised by its reactivity towards acid‐catalysed cyclisations and its thermal lability in a Cope rearrangement to β‐elemene. Similar observations have been made for other germacrenes, suggesting that the high ring strain associated with the 10‐membered ring in these systems may be a strong driving force for the observed reactions leading to much less strained compounds with 6‐membered rings. Germacrene A is of central importance in sesquiterpene biosynthesis and this Review covers the biosynthetic derivatives, the absolute configurations and the natural sources. For more information, see the Review by Dickschat et al. on page 17318.