A Nozaki-Hiyama-Kishi Ni(II)/Cr(II) coupling approach to the phomactins.
[reaction: see text] Through a unified synthetic strategy, appropriately functionalized bicyclic starting materials can be elaborated via Ni(II)/Cr(II) macrocylization to [9.3.1] bicycles. Elaboration of these core structures allows access to phomactin C/D analogues and establishes the first synthetic approach to phomactin A affording an intact octahydrochromene/macrocyclic ring system.
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Department of Chemistry, Michigan State University, East Lansing, Michigan 48824, USA.
Maleczka
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D000818:Animals; D002857:Chromium / Q000737:chemistry; D004852:Epoxy Compounds; D005658:Fungi / Q000737:chemistry; D006146:Guanidines / Q000138:chemical synthesis*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D006801:Humans; D008386:Marine Biology; D009532:Nickel / Q000737:chemistry; D010972:Platelet Activating Factor / Q000037:antagonists & inhibitors; D010975:Platelet Aggregation Inhibitors / Q000138:chemical synthesis; D013141:Spiro Compounds / Q000138:chemical synthesis*
D004852:Epoxy Compounds; D006146:Guanidines; D006576:Heterocyclic Compounds, 4 or More Rings; D010972:Platelet Activating Factor; D010975:Platelet Aggregation Inhibitors; D013141:Spiro Compounds; C103093:phomactin D; D002857:Chromium; C413206:phomactin A; C438976:palau'amine; D009532:Nickel