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Synthesis of Antirrhinolide, a New Lactone from Antirrhinum Majus
Author(s) -
Franzyk Henrik,
Frederiksen Signe M.,
Rosendal Jensen Søren
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199808)1998:8<1665::aid-ejoc1665>3.0.co;2-d
Subject(s) - scrophulariaceae , chemistry , lactone , antirrhinum majus , iridoid , stereochemistry , glycoside , botany , biochemistry , biology , gene
In addition to the known iridoid glucosides antirrhinoside ( 1 ), antirrhide ( 3 ), linarioside ( 5 ) and chaenorrhinoside ( 6 ), a novel nonglucosidic iridoid lactone was isolated in trace amount from Antirrhinum majus (Scrophulariaceae). This lactone, named antirrhinolide ( 4a ) was synthesised from 5,6‐ O ‐isopropylidene‐dihydroantirrhinoside aglucone ( 7 ) in two steps. Thus, its absolute stereochemistry was proven unequivocally.