Synthesis of (-)-Piperitylmagnolol Featuring ortho-Selective Deiodination and Pd-Catalyzed Allylation.
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.
Department of Bioengineering, Tokyo Institute of Technology , Box B-52, Nagatsuta-cho 4259, Midori-ku, Yokohama 226-8501, Japan.
Atsushi
A
Ikoma
Department of Bioengineering, Tokyo Institute of Technology , Box B-52, Nagatsuta-cho 4259, Midori-ku, Yokohama 226-8501, Japan.
Narihito
N
Ogawa
Department of Bioengineering, Tokyo Institute of Technology , Box B-52, Nagatsuta-cho 4259, Midori-ku, Yokohama 226-8501, Japan.
Daiki
D
Kondo
Department of Bioengineering, Tokyo Institute of Technology , Box B-52, Nagatsuta-cho 4259, Midori-ku, Yokohama 226-8501, Japan.
Hiroki
H
Kawada
Department of Bioengineering, Tokyo Institute of Technology , Box B-52, Nagatsuta-cho 4259, Midori-ku, Yokohama 226-8501, Japan.
Yuichi
Y
Kobayashi