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Natural Product Letters Volume 14, 1999 - Issue 1
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Original Articles

A New Synthesis of (+)-Bakuchiol

Sakurako Sakakiyama Department of Chemical and Biological Sciences, Faculty of Science, Japan Women's University, Mejirodai 2-8-1 Bunkyoku, Tokyo, 112-0015, Japan
,
Kayoko Yamamoto Department of Chemical and Biological Sciences, Faculty of Science, Japan Women's University, Mejirodai 2-8-1 Bunkyoku, Tokyo, 112-0015, Japan
&
Morio Asaoka Department of Chemical and Biological Sciences, Faculty of Science, Japan Women's University, Mejirodai 2-8-1 Bunkyoku, Tokyo, 112-0015, Japan
Pages 1-4 | Received 07 Oct 1998, Published online: 04 Oct 2006

References

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  • (-)-2:1H nmr (CDCl3) δ=0.11 (s, 9H), 1.10 (s, 3H), 1.0–1.66 (m, 1H), 2.30 (s, 3H), 1.66–2.83 (m, 4H), 4.73 (m, 1H), 4.97 (br s, 1H), 5.27 (br s, 1H), 5.17–6.0 (m, 1H), 7.02 (d, J=8 Hz, 2H), 7.20 (d, J=8Hz, 2H); 13C nmr (CDCl3) δ=0.4, 21.2, 22.5, 29.8, 34.8, 39.4, 46.9, 117.3, 119.4, 124.8, 130.5, 134.2, 135.3, 140.2, 164.3, 199.6; IR(KBr) 1590 (C˭C), 1655 (C˭O) m−1; HRMS calcd for C20H28OSSi 344.1629, found 344.1633
  • Tuda , T. , Hasyashi , T. , Satomi , H. , Kawamoto , T. and Saegusa , T. 1986 . J. Org. Chem. , 51 : 537 – 540 .
  • Hudlric , P. F. , Hudlric , A. M. , Nagendrappa , G. , Yimenu , T. , Zellers , E. T. , Zellers , E. T. and Chin , E. 1980 . J. Am. Chem. Soc. , 102 : 6894 – 6898 .
  • (+)–8:1H nmr (400 MHz in CDCl3) δ=1.19 (s, 3H), 1.83–1.87 (m, 2H), 2.29–2.33 (m, 2H), 3.63 (s, 3H), 3.80 (s, 3H), 5.02–5.08 (m, 2H), 5.84 (dd, J=11 and 17Hz, 1H), 6.01 (d, J=16Hz, 1H), 6.28 (d, J=16Hz, 1H), 6.84 (d., I=9Hz, 2H), 7.29 (d, J=9Hz, 2H); 13C nmr (100 MHz in CDCl3) δ= 23.2, 29.6, 35.4, 42.0, 51.4, 55.2, 112.6, 113.8, 127.2, 127.3, 130.2, 134.4, 144.9, 158. 174.3; IR(neat) 1600 (C˭C), 1725 (C˭O) cm−1; HRMS calcd for C17H22O3 274.1568, found. 274.1569
  • The spectral (1H nmr, 13C nmr, IR, and HRMS) data are in full agreement with those of (e)-9.If 3325–3326

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