Synthesis of the N-((1E)-alkenyl)-(2Z,4Z)-heptadienamide side chain of salicylihalamide A and apicularens A and B.
[reaction: see text] The unstable N-((1E)-alkenyl)-(2Z,4Z)-heptadienamide side chain of salicylihalamide A (1) and apicularens A and B (3 and 4) has been prepared in one pot by the addition of (1Z,3Z)-hexadienylcuprate, prepared in situ from EtLi, CuBr.SMe2, and acetylene, to a (1 E)-alkenyl isocyanate.
Snider
B B
BB
Department of Chemistry, Brandeis University, Waltham, Massachusetts 02254-9110, USA. snider@brandeis.edu
Song
F
F
D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry*; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry*; D018942:Macrolides; D009161:Mycobacterium / Q000737:chemistry; D011161:Porifera / Q000737:chemistry
D000900:Anti-Bacterial Agents; D000903:Antibiotics, Antineoplastic; D000970:Antineoplastic Agents; D019086:Bridged Bicyclo Compounds, Heterocyclic; D018942:Macrolides; C117813:apicularen A; C117814:apicularen B; C410986:salicylihalamide A