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Keywords:

  • acyliminium ions;
  • biotin;
  • cyclizations;
  • silyl enol ethers;
  • total syntheses
Thumbnail image of graphical abstract

Irrespective of the geometry of the double bond the configuration of the newly formed chiral center is established by the existing adjacent stereogenic center in the Lewis acid catalyzed cyclization of the N-acyliminium silyl enol ether intermediate 1. This step is the key transformation in a new, concise total synthesis of D-( + )-biotin. R [DOUBLE BOND] protecting group.