Total synthesis of (−)-nakadomarin A: alkyne ring-closing metathesis

• Published in: Tetrahedron letters 2011-11, Vol.52 (46), p.6094-6097
• Main Authors: Jakubec, Pavol, Kyle, Andrew F., Calleja, Jonás, Dixon, Darren J.
• Format: Article
• Language: English
• Subjects: Alkyne ring-closing metathesis; Alkynes; Cascade; Cascade control; Catalysis; Catalysts: preparations and properties; Chemistry; Decomposition reactions; Exact sciences and technology; Furans; General and physical chemistry; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Iminium ion; Metathesis; Michael addition; Nakadomarin A; Nitro-Mannich reaction; Organic chemistry; Organocatalysis; Preparations and properties; Reduction; Stereoselective synthesis; Synthesis (chemistry); Tetrahedrons; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; Total synthesis
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2011.09.016

A 13-step, highly stereoselective synthesis of (−)-nakadomarin A has been achieved using the combination of a bifunctional organocatalyst controlled Michael addition, a nitro-Mannich/lactamization cascade, an alkyne ring-closing metathesis/syn-reduction, and furan/iminium ion cyclization/reduction as key steps. A 13-step, highly stereoselective synthesis of (−)-nakadomarin A has been achieved using the combination of a bifunctional organocatalyst controlled Michael addition, a nitro-Mannich/lactamization cascade, an alkyne ring-closing metathesis/syn-reduction, and furan/iminium ion cyclization/reduction as key steps.