A biomimetic synthesis of (±)-basiliolide B.

نویسندگان

  • Long Min
  • Yang Zhang
  • Xuefeng Liang
  • Junrong Huang
  • Wenli Bao
  • Chi-Sing Lee
چکیده

A highly diastereoselective and practical biomimetic total synthesis of (±)-basiliolide B has been achieved through the study of the two proposed biosynthetic pathways (O-methylation and O-acylation) for the unprecedented 7-methoxy-4,5-dihydro-3H-oxepin-2-one (C ring). The synthesis featured a cyclopropanation/ring opening strategy for establishing the stereogenic centers at C8 and C9, a biomimetic 2-pyrone Diels-Alder cycloaddition for the synthesis of the ABD ring system, and finally a highly efficient biomimetic intramolecular O-acylation for the C ring formation. This result provides an important perspective on the biosynthetic origin of the unprecedented 7-membered acyl ketene acetal moiety of the C ring.

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عنوان ژورنال:
  • Angewandte Chemie

دوره 53 42  شماره 

صفحات  -

تاریخ انتشار 2014