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Synlett 2008(16): 2459-2460  
DOI: 10.1055/s-2008-1078052
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Total Synthesis of (+)-Dodoneine

Aurélia Dittoo, Véronique Bellosta, Janine Cossy*
Laboratoire de Chimie Organique, ESPCI ParisTech, CNRS, 10 rue Vauquelin, 75231 Paris Cedex 05, France
Fax: +33(1)40794660; e-Mail: janine.cossy@espci.fr;
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Publication History

Received 12 June 2008
Publication Date:
12 September 2008 (online)

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Abstract

An eight-step synthesis of (+)-dodoneine was achieved from methyl 3-(4-hydroxyphenyl)propionate.

Key words

total synthesis - dodoneine - allyltitanation - cross­metathesis - 1,4-addition

    References and Notes

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8

Compound 9: R f = 0.23 (PE-EtOAc, 2:8); [α] d ²0 +48.1
(c = 0.34, CHCl3) {Lit. [¹] [α] d ²0 +40.2 (c = 0.40, CHCl3)}. IR (neat): 3311, 2920, 1698, 1515 cm-¹. ¹H NMR (400 MHz, CDCl3): δ = 7.05 (app dt, J = 8.5, 2.5 Hz, 2 H), 6.88 (app dt, J = 9.5, 4.1 Hz, 1 H), 6.76 (app dt, J = 8.5, 2.5 Hz, 2 H), 6.02 (dt, J = 9.8, 1.9 Hz, 1 H), 5.32 (br s, 1 H), 4.65 (dddd, J = 7.7, 7.7, 7.7, 5.3 Hz, 1 H), 3.87 (m, 1 H), 2.67 (m, 2 H), 2.38 (m, 2 H), 2.00 (dt, J = 15.7, 8.2 Hz, 1 H), 1.90 (br s, 1 H, OH), 1.79 (m, 3 H). ¹³C NMR (100 MHz, CDCl3): δ = 164.6 (s), 154.3 (s), 145.8 (d), 133.9 (s), 129.8 (2 × d), 121.5 (d), 115.7 (2 × d), 77.4 (d), 69.0(d), 42.4 (t), 39.7 (t), 31.2 (t), 29.8 (t). MS (EI, 70 eV): m/z (%) = 262 (5), 150 (2), 133 (10), 120 (9), 108 (27), 107 (100), 94 (14), 77 (49), 67 (23), 53 (22). HRMS (ESI): m/z [M + Na]+ calcd for C15H18O4Na: 285.10987; found: 285.10973.