Stereoselective Synthesis of a Bicyclic Norsesquiterpene Backbone – A Possible Route to Nardosinane Derivatives. Issue 31 (17th September 2013)

• Record Type: Journal Article
• Authors: Selaïmia‐Ferdjani, 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
• Is Part Of: European journal of organic chemistry. Issue 31(2013)
• Page Start: 7083
• Page End: 7094
• Publication Date: 2013-09-17
• Subjects: Synthesis design -- Aldol reactions -- Epoxidation -- Diastereoselectivity -- Terpenoids; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201301087
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: We have developed an efficient diastereoselective synthetic route towards a nardosinane sesquiterpene scaffold. The strategy used a key bicyclic diene intermediate11a, and allowed access to valuable polyoxygenated sesquiterpenes21 and22, which may be regarded as analogues of the natural sesquiterpenes laevinol B and fulvol acetate, respectively. Abstract : A stereoselective approach towards the synthesis of a (nor)nardosinane sesquiterpene scaffold is reported, going via a key dienic precursor. The synthetic route involved the introduction of four contiguous stereogenic centres onto the bicyclic backbone, and the diene intermediate was obtained in 14 % yield over seven steps from ( S )‐carvone.