title: Synthesis of phantasmidine.
abstract: Reaction of 6-chloro-2-fluoro-3-pyridineacetamide with 1,2-bis(trimethylsilyloxy)cyclobutene in ether saturated with hydrogen chloride afforded the keto amide in 85% yield. In the key step, treatment of the keto amide with aqueous KOH in t-BuOH resulted in a tandem intramolecular aldol reaction-intramolecular nucleophilic aromatic substitution sequence to give the tetracylic lactam in 46% yield. Reduction of the lactam with BH(3) in THF gave phantasmidine in 67% yield.
authors.affiliation: Department of Chemistry MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
authors.forename: Quan
authors.initials: Q
authors.lastname: Zhou
authors.forename: Barry B
authors.initials: BB
authors.lastname: Snider
mesh_terms: D000664:Amphibian Venoms / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D001001:Anura; D003503:Cyclobutanes / Q000737:chemistry*; D006572:Heterocyclic Compounds, Bridged-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D006851:Hydrochloric Acid; D015394:Molecular Structure; D011725:Pyridines / Q000737:chemistry*; D013237:Stereoisomerism; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
chemical_list: C556388:1,2-bis(trimethylsilyloxy)cyclobutene; C556387:6-chloro-2-fluoro-3-pyridineacetamide; D000664:Amphibian Venoms; D003503:Cyclobutanes; D006572:Heterocyclic Compounds, Bridged-Ring; D006846:Hydrocarbons, Halogenated; D011725:Pyridines; D014297:Trimethylsilyl Compounds; C548947:phantasmidine; D006851:Hydrochloric Acid