Premium
Total Synthesis of Aignopsanes, A Class of Sesquiterpenes: (+)‐Aignopsanoic Acid A, (−)‐Methyl Aignopsanoate A, and (−)‐Isoaignopsanoic A
Author(s) -
Bürki Cédric,
Bonjoch Josep,
Bradshaw Ben,
Villa Giorgio,
Renaud Philippe
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201404766
Subject(s) - sesquiterpene , absolute configuration , total synthesis , enantiomer , stereochemistry , chemistry , transformation (genetics) , biochemistry , gene
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.