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Stereoselective Synthesis of a Bicyclic Norsesquiterpene Backbone – A Possible Route to Nardosinane Derivatives
Author(s) -
SelaïmiaFerdjani Ouassila,
Kar Anirban,
Chavan Sambhaji P.,
Horeau Maxime,
Viault Guillaume,
Pouessel Jacky,
Guillory Xavier,
Blot Virginie,
Tessier Arnaud,
Planchat Aurelien,
Jacquemin Denis,
Dubreuil Didier,
Pipelier Muriel
Publication year - 2013
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.201301087
Subject(s) - bicyclic molecule , chemistry , sesquiterpene , stereoselectivity , stereochemistry , total synthesis , diene , combinatorial chemistry , organic chemistry , catalysis , natural rubber
We have developed an efficient diastereoselective synthetic route towards a nardosinane sesquiterpene scaffold. The strategy used a key bicyclic diene intermediate 11a , and allowed access to valuable polyoxygenated sesquiterpenes 21 and 22 , which may be regarded as analogues of the natural sesquiterpenes laevinol B and fulvol acetate, respectively.