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  • Title: Total synthesis of aignopsanes, a class of sesquiterpenes: (+)-aignopsanoic acid A, (-)-methyl aignopsanoate A, and (-)-isoaignopsanoic A.
    Author: Bürki C, Bonjoch J, Bradshaw B, Villa G, Renaud P.
    Journal: Chemistry; 2015 Jan 02; 21(1):395-401. PubMed ID: 25346030.
    Abstract:
    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.
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