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An Improved Method for the endo ‐Fusion of Five‐Membered Ring Lactones to the Bornane Ring System
Author(s) -
Knollmüller Max,
Gärtner Peter,
Ferencic Mathias,
Noe Christian R.,
Mereiter Kurt
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(199811)1998:11<2507::aid-ejoc2507>3.0.co;2-8
Subject(s) - chemistry , thionyl chloride , lactol , lactone , ring (chemistry) , stereochemistry , yield (engineering) , tributyltin hydride , reagent , reactivity (psychology) , organic chemistry , chloride , medicine , materials science , alternative medicine , pathology , metallurgy
endo ‐Fused lactone 3 was obtained in high yield from the camphoracetic acid 2 with thionyl chloride and a subsequent reduction of intermediate 5 with tributyltin hydride. The structure of 5 was elaborated and some aspects of the mechanism of its formation and reactivity were investigated. Lactone 3 serves as key intermediate for lactol 1 which is a useful reagent in racemate resolution and asymmetric synthesis.