- Synthesis of (-)-Piperitylmagnolol Featuring ortho-Selective Deiodination and Pd-Catalyzed Allylation
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A 1,4-addition strategy using an enone and a copper reagent was studied for the synthesis of (-)-piperitylmagnolol. A MOM-protected biphenol copper reagent was added to BF3·OEt2-activated 4-isopropylcyclohexenone, whereas 1,4-addition of protected monophenol reagents possessing an allyl group was found to be unsuccessful. The allyl group was later attached to the p-,p′-diiodo-biphenol ring by Pd-catalyzed coupling with allylborate. The aforementioned iodide was synthesized using a new method for ortho-selective deiodination of o-,p-diiodophenols.
- Ikoma, Atsushi,Ogawa, Narihito,Kondo, Daiki,Kawada, Hiroki,Kobayashi, Yuichi
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supporting information
p. 2074 - 2077
(2016/06/01)
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- Synthesis of Thyroid Hormone Analogues. Part 3. Iodonium Salt Approaches to SK&F L-94901
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The key step in the synthesis of L-3,5-dibromo-3'--thyronine, SK&F L-94901 (1), a novel, selective, and potent thyromimetic, is the formation of the hindered diaryl ether moiety.This paper describes an investigation into the formation of the required diaryl ether by copper-catalysed reaction both of symmetrical iodonium salts (2a) and (10) and mixed iodonium salts (2b-e) with protected dibromotyrosine (5).The importance of the counter-ion of the iodonium salt is discussed.This work is extended to a large-scale synthesis of SK&F L-94901 (1).
- Hickey, Deirdre M. B.,Leeson, Paul D.,Novelli, Riccardo,Shah, Virendra P.,Burpitt, Brian E.,et al.
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p. 3103 - 3112
(2007/10/02)
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