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Synthetic Studies Directed Towards Various Homologues of Natural Sesquiterpene‐Coumarin Ethers: The Domino Approach
Author(s) -
Corbu Andrei,
Castro Juan M.,
Aquino Maurizio,
Gandara Zoila,
Retailleau Pascal,
Arseniyadis Siméon
Publication year - 2010
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/ejoc.200901352
Subject(s) - chemistry , domino , diastereomer , coumarin , sesquiterpene , stereochemistry , substituent , terpene , adduct , ring (chemistry) , organic chemistry , catalysis
A domino‐based strategy was used to construct analogues containing the basic skeleton of the monocyclic sesquiterpene‐coumarin ethers galbanic acid ( 1 ) and secodrial ( 3 ), through conversion of the domino adduct 19 into 10 and 11 , chosen as representative targets. 1 H NMR patterns, corroborated by X‐ray crystallographic analysis for two of the four possible diastereomeric arrangements of the six‐membered B‐ring common to various A‐ seco terpenes, have been determined. The observed trends help in the design of substituent combinations that provide a tool for diastereomeric recognition, depending on the cis / trans arrangement of the adjacent methyl groups and the adopted conformations.