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Stereocontrolled Formation of Annelated Cyclopentanes by Intramolecular Hetero‐Diels–Alder Reaction. Synthesis of Deoxyloganin from Citronellal
Author(s) -
Tietze Lutz F.,
Denzer Horst,
Holdgrün Xenia,
Neumann Manfred
Publication year - 1987
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198712951
Subject(s) - cyclopentanes , intramolecular force , chemistry , cycloaddition , intermolecular force , citronellal , adduct , stereochemistry , pyran , stereoselectivity , diels–alder reaction , derivative (finance) , catalysis , organic chemistry , molecule , financial economics , economics
An astonishingly highly induced diastercoselectivity (>98%) characterizes the intermolecular cycloaddition of the adduct of 1 and 2 . The cis coupled cyclopenta[c]pyran derivative 3 is formed, which could be converted in six steps into the deoxyloganin 4 . Compound 4 is of interest as a precursor for the biosynthesis of alkaloids.