Stereoselective Synthesis of a Bicyclic Norsesquiterpene Backbone – A Possible Route to Nardosinane Derivatives | Zendy

SelaïmiaFerdjani Ouassila | Zendy; Kar Anirban | Zendy; Chavan Sambhaji P. | Zendy; Horeau Maxime | Zendy; Viault Guillaume | Zendy; Pouessel Jacky | Zendy; Guillory Xavier | Zendy; Blot Virginie | Zendy; Tessier Arnaud | Zendy; Planchat Aurelien | Zendy; Jacquemin Denis | Zendy; Dubreuil Didier | Zendy; Pipelier Muriel | Zendy

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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.

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