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Keywords:

  • catalysis;
  • cyclization;
  • natural products;
  • pectenotoxin;
  • spiroketals
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Concepts: The formation of stereochemically defined bis-THF units through a double cyclization and a hydride-shift-initiated route to spiroketals is described (see scheme; Xc=chiral auxiliary). The resulting sequence has been used in a synthesis of the C1–16 fragment of the naturally occurring antitumor agent pectenotoxin-4.