Total Synthesis of Aignopsanes, A Class of Sesquiterpenes: (+)‐Aignopsanoic Acid A, (−)‐Methyl Aignopsanoate A, and (−)‐Isoaignopsanoic A. Issue 1 (24th October 2014)

• Record Type: Journal Article
• Authors: Bürki, Cédric; Bonjoch, Josep; Bradshaw, Ben; Villa, Giorgio; Renaud, Philippe
• Is Part Of: Chemistry. Volume 21:Issue 1(2015)
• Page Start: 395
• Page End: 401
• Publication Date: 2014-10-24
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201404766
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>A general strategy for the synthesis of aignopsanes, a new family of sesquiterpene natural products of marine origin, is presented. The total synthesis of (+)‐aignopsanoic acid A (<bold>1</bold>), (−)‐methyl aignopsanoate A (<bold>2</bold>), and (−)‐isoaignopsanoic A (<bold>3</bold>) has been achieved and their absolute configuration confirmed. (+)‐Microcionin‐1 (<bold>4</bold>), a structurally related furanosesquiterpene isolated in both enantiomeric forms from marine sponges, was also synthesized and its absolute configuration established in an unambiguous way. Interestingly, we report that (+)‐microcionin‐1 (<bold>4</bold>), can be converted by a simple oxidation process to aignopsanoic acid A (<bold>1</bold>). This transformation supports the hypothesis that (+)‐microcionin‐1 (<bold>4</bold>) may be an intermediate in the biosynthesis of aignopsanes.</p> </abstract>