Total synthesis of (-)-salicylihalamide A.
[see structure]. A 16-step synthesis of the novel cytotoxin salicylihalamide A (1E) has been achieved in 3.3% overall yield using ring closing metathesis to generate the macrolide and addition of (1Z,3Z)-hexadienylcuprate (2), which was generated in situ from ethylcuprate and acetylene, to alkenyl isocyanate 3 to form the side chain.
Snider
B B
BB
Department of Chemistry MS015, Brandeis University, Waltham, Massachusetts 02454-9110, USA. snider@bramdeis.edu
Song
F
F
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D019086:Bridged Bicyclo Compounds, Heterocyclic; C410986:salicylihalamide A