2‐Pyrones with a chiral branched allylic silyl ether substituent underwent intramolecular Diels–Alder reactions with remarkably high π‐facial‐ and endo‐selectivities. The resulting diastereomerically and enantiomerically pure cycloadducts were transformed into the natural products (+)‐lycopladine A and (−)‐lycoposerramine R.
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