Total Synthesis of Aignopsanes, A Class of Sesquiterpenes: (+)-Aignopsanoic Acid A, (−)-Methyl Aignopsanoate A, and (−)-Isoaignopsanoic A

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

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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.

Item Type:

Journal Article (Original Article)

Division/Institute:

08 Faculty of Science > Departement of Chemistry and Biochemistry

UniBE Contributor:

Bürki, Cédric and Renaud, Philippe

Subjects:

500 Science > 570 Life sciences; biology
500 Science > 540 Chemistry

ISSN:

0947-6539

Publisher:

Wiley-VCH

Language:

English

Submitter:

Philippe Renaud

Date Deposited:

22 Jan 2016 11:18

Last Modified:

26 Jan 2016 15:26

Publisher DOI:

10.1002/chem.201404766

BORIS DOI:

10.7892/boris.74641

URI:

https://boris.unibe.ch/id/eprint/74641

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