Ontology highlight
ABSTRACT:
SUBMITTER: Kong K
PROVIDER: S-EPMC3256008 | biostudies-literature | 2011 Dec
REPOSITORIES: biostudies-literature
Journal of the American Chemical Society 20111116 49
The first total synthesis of the marine toxin (-)-gymnodimine (1) has been accomplished in a convergent manner. A highly diastereo- and enantioselective exo-Diels-Alder reaction catalyzed by a bis-oxazoline Cu(II) catalyst enabled rapid assembly of the spirocyclic core of gymnodimine. The preparation of the tetrahydrofuran fragment utilized a chiral auxiliary based anti-aldol reaction. Two major fragments, spirolactam 56 and tetrahydrofuran 55, were then coupled through an efficient Nozaki-Hiyam ...[more]