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

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...

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Published in:Angewandte Chemie International Edition 2022-10, Vol.61 (42), p.e202212016-n/a
Main Authors: Sim, Kyu‐Hyun, ul Ansari, Thameem, Park, Yong‐Gyu, Jeong, Yeolib, Oh, Sang‐Ha, Min, Hye‐Won, Jeon, Da‐Yoon, Kim, Hyunwoo, Cho, Cheon‐Gyu
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Language:English
Subjects:
Cascade Reactions
Cycloaddition
Diels-Alder reactions
Diels–Alder Reaction
Natural products
Pyridines
Stereoselectivity
Stille Cross-Coupling
Total Synthesis
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cited_by cdi_FETCH-LOGICAL-c3506-eb284b90d975076d25dd855f979736d20cbbf95184ed3d6ce576f3690007a9323
cites cdi_FETCH-LOGICAL-c3506-eb284b90d975076d25dd855f979736d20cbbf95184ed3d6ce576f3690007a9323
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container_issue 42
container_start_page e202212016
container_title Angewandte Chemie International Edition
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creator Sim, Kyu‐Hyun
ul Ansari, Thameem
Park, Yong‐Gyu
Jeong, Yeolib
Oh, Sang‐Ha
Min, Hye‐Won
Jeon, Da‐Yoon
Kim, Hyunwoo
Cho, Cheon‐Gyu
description 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. Highly efficient asymmetric intramolecular Diels–Alder reactions of 3‐substituted 2‐pyrones were combined with C3‐selective Stille cross‐coupling reactions in a tandem fashion. The resulting diastereomerically and enantiomerically pure cycloadducts were successfully converted into (+)‐lycopladine A and lycoposerramine R.
doi_str_mv 10.1002/anie.202212016
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source Wiley-Blackwell Read & Publish Collection
subjects Cascade Reactions
Cycloaddition
Diels-Alder reactions
Diels–Alder Reaction
Natural products
Pyridines
Stereoselectivity
Stille Cross-Coupling
Total Synthesis
title 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
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