A Regio- and Diastereoselective Stille Coupling/Intramolecular Diels-Alder Cascade for the Generation of Fused Pyridines and Application in the Synthesis of (+)-Lycopladine A and (-)-Lycoposerramine R

  • Sim, Kyu-Hyun
  • ul Ansari, Thameem
  • Park, Yong-Gyu
  • Jeong, Yeolib
  • Oh, Sang-Ha
  • ... Cho, Cheon-Gyu
  • 외 3명
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초록

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

키워드

Cascade ReactionsCycloadditionDiels-Alder ReactionStille Cross-CouplingTotal SynthesisHIGHLY SUBSTITUTED PYRIDINES2+2+2 CYCLOADDITIONALLYLIC ETHERIFICATION3,5-DIBROMO-2-PYRONECONSTRUCTIONCYCLIZATIONS1-AZADIENESALCOHOLSOXIMESMILD
제목
A Regio- and Diastereoselective Stille Coupling/Intramolecular Diels-Alder Cascade for the Generation of Fused Pyridines and Application in the Synthesis of (+)-Lycopladine A and (-)-Lycoposerramine R
저자
Sim, Kyu-Hyunul Ansari, ThameemPark, Yong-GyuJeong, YeolibOh, Sang-HaMin, Hye-WonJeon, Da-YoonKim, HyunwooCho, Cheon-Gyu
DOI
10.1002/anie.202212016
발행일
2022-09
유형
Article; Early Access
저널명
Angewandte Chemie - International Edition
61
42
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1 ~ 5