Total Synthesis of Aignopsanes, A Class of Sesquiterpenes: (+)-Aignopsanoic Acid A, (−)-Methyl Aignopsanoate A, and (−)-Isoaignopsanoic A
Data(s) |
2014
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Resumo |
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 (1), (−)-methyl aignopsanoate A (2), and (−)-isoaignopsanoic A (3) has been achieved and their absolute configuration confirmed. (+)-Microcionin-1 (4), 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 (4), can be converted by a simple oxidation process to aignopsanoic acid A (1). This transformation supports the hypothesis that (+)-microcionin-1 (4) may be an intermediate in the biosynthesis of aignopsanes. |
Formato |
application/pdf |
Identificador |
http://boris.unibe.ch/74641/1/395_ftp.pdf Bürki, Cédric; Bonjoch, Josep; Bradshaw, Ben; Villa, Giorgio; Renaud, Philippe (2014). Total Synthesis of Aignopsanes, A Class of Sesquiterpenes: (+)-Aignopsanoic Acid A, (−)-Methyl Aignopsanoate A, and (−)-Isoaignopsanoic A. Chemistry - a European journal, 21(1), pp. 395-401. Wiley-VCH 10.1002/chem.201404766 <http://dx.doi.org/10.1002/chem.201404766> doi:10.7892/boris.74641 info:doi:10.1002/chem.201404766 urn:issn:0947-6539 |
Idioma(s) |
eng |
Publicador |
Wiley-VCH |
Relação |
http://boris.unibe.ch/74641/ |
Direitos |
info:eu-repo/semantics/restrictedAccess |
Fonte |
Bürki, Cédric; Bonjoch, Josep; Bradshaw, Ben; Villa, Giorgio; Renaud, Philippe (2014). Total Synthesis of Aignopsanes, A Class of Sesquiterpenes: (+)-Aignopsanoic Acid A, (−)-Methyl Aignopsanoate A, and (−)-Isoaignopsanoic A. Chemistry - a European journal, 21(1), pp. 395-401. Wiley-VCH 10.1002/chem.201404766 <http://dx.doi.org/10.1002/chem.201404766> |
Palavras-Chave | #570 Life sciences; biology #540 Chemistry |
Tipo |
info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion PeerReviewed |