A Novel Biomimetic Route to the 3‐Acyl‐5‐hydroxy‐3‐pyrrolin‐2‐one and 3‐Acyl‐3,4‐epoxy‐5‐hydroxypyrrolidin‐2‐one Ring Systems.

Abstract

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Total Synthesis of (−)-FD-838 and (−)-Cephalimysin A

“…Our initial synthetic efforts were rewarded by the total synthesis of (±)-berkeleyamide D (3, 10 longest linear steps). 14 Keys to this initial report were the Snider-type tandem epoxidations 15 and the biosynthetically inspired late-stage spirocyclization reaction. We subsequently planned to apply lessons learned from these synthetic studies to the total synthesis of structurally more complex azaspirene (4).…”

“…Detailed reaction mechanism for the transformation of aldehyde 21 to spirocycle 22 that involves Snider-type tandem oxidations is presented in Scheme 3 15. Intramolecular aldol reaction of aldehyde 21 and subsequent β-hydroxy elimination of the resulting intermediate 24 would yield enone derivative 25.…”