Asymmetric total synthesis of (+)-carneic acid A and structure revision of its natural form
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作者:
Yamakoshi, Shuhei
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Waseda Univ, Fac Sci & Engn, Dept Chem & Biochem, Shinjuku Ku, Tokyo 1698555, JapanWaseda Univ, Fac Sci & Engn, Dept Chem & Biochem, Shinjuku Ku, Tokyo 1698555, Japan
Yamakoshi, Shuhei
[1
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Hayashi, Nobuyuki
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Waseda Univ, Fac Sci & Engn, Dept Chem & Biochem, Shinjuku Ku, Tokyo 1698555, JapanWaseda Univ, Fac Sci & Engn, Dept Chem & Biochem, Shinjuku Ku, Tokyo 1698555, Japan
Hayashi, Nobuyuki
[1
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Suzuki, Takahiro
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Waseda Univ, Fac Sci & Engn, Dept Chem & Biochem, Shinjuku Ku, Tokyo 1698555, JapanWaseda Univ, Fac Sci & Engn, Dept Chem & Biochem, Shinjuku Ku, Tokyo 1698555, Japan
Suzuki, Takahiro
[1
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Nakada, Masahisa
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Waseda Univ, Fac Sci & Engn, Dept Chem & Biochem, Shinjuku Ku, Tokyo 1698555, JapanWaseda Univ, Fac Sci & Engn, Dept Chem & Biochem, Shinjuku Ku, Tokyo 1698555, Japan
Nakada, Masahisa
[1
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[1] Waseda Univ, Fac Sci & Engn, Dept Chem & Biochem, Shinjuku Ku, Tokyo 1698555, Japan
This Letter describes the asymmetric total synthesis of (+)-carneic acid A via the stereoselective IMDA reaction of (E,E,E)-triene, which was prepared from the commercially available methyl (S)-3-hydroxy-2-methylpropionate. By this asymmetric total synthesis, we verified that the reported absolute structure of naturally occurring carneic acid A must be revised. (C) 2009 Elsevier Ltd. All rights reserved.
机构:
Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, 501 Haike Rd,Zhangjiang Hitech Pk, Shanghai 201203, Peoples R ChinaChinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, 501 Haike Rd,Zhangjiang Hitech Pk, Shanghai 201203, Peoples R China
Zheng, Yong
Song, Wei-Bin
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Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, 501 Haike Rd,Zhangjiang Hitech Pk, Shanghai 201203, Peoples R ChinaChinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, 501 Haike Rd,Zhangjiang Hitech Pk, Shanghai 201203, Peoples R China
Song, Wei-Bin
Xuan, Li-Jiang
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Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, 501 Haike Rd,Zhangjiang Hitech Pk, Shanghai 201203, Peoples R ChinaChinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, 501 Haike Rd,Zhangjiang Hitech Pk, Shanghai 201203, Peoples R China
机构:
Chiba Univ, Grad Sch Pharmaceut Sci, Chuo Ku, 1-8-1 Inohana, Chiba 2608675, JapanChiba Univ, Grad Sch Pharmaceut Sci, Chuo Ku, 1-8-1 Inohana, Chiba 2608675, Japan
Wu, Siyuan
Harada, Shinji
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Chiba Univ, Grad Sch Pharmaceut Sci, Chuo Ku, 1-8-1 Inohana, Chiba 2608675, Japan
Chiba Univ, Mol Chiral Res Ctr, Inage Ku, 1-33 Yayoi Cho, Chiba 2638522, JapanChiba Univ, Grad Sch Pharmaceut Sci, Chuo Ku, 1-8-1 Inohana, Chiba 2608675, Japan
Harada, Shinji
Morikawa, Takahiro
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Chiba Univ, Grad Sch Pharmaceut Sci, Chuo Ku, 1-8-1 Inohana, Chiba 2608675, JapanChiba Univ, Grad Sch Pharmaceut Sci, Chuo Ku, 1-8-1 Inohana, Chiba 2608675, Japan
Morikawa, Takahiro
Nishida, Atsushi
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Chiba Univ, Grad Sch Pharmaceut Sci, Chuo Ku, 1-8-1 Inohana, Chiba 2608675, Japan
Chiba Univ, Mol Chiral Res Ctr, Inage Ku, 1-33 Yayoi Cho, Chiba 2638522, JapanChiba Univ, Grad Sch Pharmaceut Sci, Chuo Ku, 1-8-1 Inohana, Chiba 2608675, Japan