Highly convergent total synthesis of (+)-acutiphycin.
An enantioselective, convergent, total synthesis of (+)-acutiphycin (18 steps, longest linear sequence from commercial materials) features the first application of an alkynyl ether as a macrolactone precursor in total synthesis, as well as the first example of an intermolecular, SmI2-mediated, Reformatsky fragment coupling reaction. The high convergence, efficiency, and modular nature of this synthesis make it amenable to the synthesis of structurally related compounds.
Moslin
Ryan M
RM
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Jamison
Timothy F
TF
D000970:Antineoplastic Agents / Q000138:chemical synthesis; D000458:Cyanobacteria / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D018942:Macrolides / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D006571:Heterocyclic Compounds; D018942:Macrolides; C515767:acutiphycin