Total synthesis of (-)-apicularen A.
Complete details of an asymmetric synthesis of apicularen (1) are described. The synthesis has been accomplished using a highly diastereo- and enantioselective [4 + 2] annulation for the assembly of the functionalized pyran core. An underdeveloped lactonization method involving an NaH promoted transesterification of an advanced intermediate bearing an aryl cyanomethyl ester was used for the macrolactonization step.
Department of Chemistry and Center for Chemical Methodology and Library Design, Metcalf Center for Science and Engineering, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA.
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D000498:Allyl Compounds / Q000138:chemical synthesis; D000970:Antineoplastic Agents / Q000138:chemical synthesis; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D018942:Macrolides / Q000138:chemical synthesis; D009231:Myxococcales / Q000737:chemistry; D012821:Silanes / Q000138:chemical synthesis; D013237:Stereoisomerism
D000498:Allyl Compounds; D000970:Antineoplastic Agents; D019086:Bridged Bicyclo Compounds, Heterocyclic; D018942:Macrolides; D012821:Silanes; C117813:apicularen A