References and Notes
<A NAME="RG40307ST-1">1</A>
Tan LT.
Phytochemistry
2007,
68:
954
<A NAME="RG40307ST-2">2</A>
Tan LT.
Márquez BL.
Gerwick WH.
J. Nat. Prod.
2002,
65:
925
<A NAME="RG40307ST-3A">3a</A>
Zampella A.
D’Auria MV.
Minale L.
Debitus C.
Tetrahedron
1997,
53:
3243
<A NAME="RG40307ST-3B">3b</A>
Sone H.
Kigosi H.
Yamada K.
J. Org. Chem.
1996,
61:
8956
<A NAME="RG40307ST-4">4</A>
Luesch H.
Yoshida WY.
Harrigan GG.
Doom JP.
Moore RE.
Paul VJ.
J. Nat. Prod.
2002,
65:
1945
<A NAME="RG40307ST-5">5</A>
Gebauer J.
Blechert S.
J. Org. Chem.
2006,
71:
2021
<A NAME="RG40307ST-6">6</A>
Gill M.
Smrdel AF.
Tetrahedron: Asymmetry
1990,
1:
453
<A NAME="RG40307ST-7">7</A>
Duthaler RO.
Hafner A.
Chem. Rev.
1992,
92:
807
<A NAME="RG40307ST-8">8</A>
Compound 3: [α]D
20 -26.2 (c 1.0, CHCl3). 1H NMR (C6D6): δ = 7.29 (d, J = 8.8 Hz, 2 H), 6.90 (d, J = 8.8 Hz, 2 H), 5.92-5.83 (m, 1 H), 5.19-5.14 (m, 2 H), 4.47 (d, J = 11.0 Hz, 1 H), 4.25 (d, J = 11.0 Hz, 1 H), 3.96 (d, J = 8.5 Hz, 1 H), 3.77 (d, J = 8.5 Hz, 1 H), 3.69 (m, 1 H), 3.41 (s, 3 H), 2.74 (m, 1 H), 1.92 (dd, J = 14.3, 3.0 Hz, 1 H), 1.85 (dd, J = 14.3, 9.3 Hz, 1 H), 1.54 (s, 3 H), 1.50 (s, 3 H), 1.40 (s, 3 H), 1.15 (d, J = 7.0 Hz, 3 H). 13C NMR (C6D6): δ = 159.7 (Cq), 141.0 (CH), 131.2 (Cq), 129.5 (CH), 114.9 (CH2), 114.1 (CH), 108.6 (Cq), 80.8 (Cq), 79.3 (CH), 75.8 (CH2), 70.7 (CH2), 54.8 (CH3), 40.5 (CH2), 39.5 (CH), 27.6 (CH3), 27.4 (CH3), 25.0 (CH3), 12.8 (CH3). ESI-HRMS: m/z calcd for C20H30NaO4: 357.2036; found 357.2035.
<A NAME="RG40307ST-9">9</A>
Denmark SE.
Heemstra JR.
Beutner GL.
Angew. Chem. Int. Ed.
2005,
44:
4682
<A NAME="RG40307ST-10">10</A>
Sato M.
Sunami S.
Sugita Y.
Kaneko C.
Heterocycles
1995,
41:
1435
<A NAME="RG40307ST-11">11</A>
Denmark SE.
Beutner GL.
J. Am. Chem. Soc.
2003,
125:
7800
<A NAME="RG40307ST-12">12</A>
CHIRALPAK AD-H (SFC), MeOH/CO2 = 8:92.
<A NAME="RG40307ST-13">13</A>
The absolute configuration of alcohol 8 was determined by hydrogenation of the terminal double bond and comparison of the
optical rotation {[α]D
20 -21.0 (c 1.0, CHCl3)} with the literature {[α]D
20 +19.8 (CHCl3) for the enantiomer}.
[10]
<A NAME="RG40307ST-14">14</A>
Compound 4: [α]D
20 +19.0 (c 1.0, CHCl3). 1H NMR (CDCl3): δ = 6.30 (dd, J = 17.8, 10.3 Hz, 1 H), 6.19 (d, J = 17.8 Hz, 1 H), 5.88 (d, J = 10.3 Hz, 1 H), 5.29 (s, 1 H), 4.34 (m, 1 H), 2.80-2.67 (m, 2 H), 2.44-2.29 (m,
2 H), 1.64 (s, 3 H), 1.63 (s, 3 H), 1.50 (br s, 1 H). 13C NMR (CDCl3): δ = 200.3 (Cq), 168.3 (Cq), 161.0 (Cq), 136.4 (CH), 129.8 (CH2), 106.7 (Cq), 95.5 (CH), 64.7 (CH), 45.1 (CH2), 40.5 (CH2), 25.5 (CH3), 24.6 (CH3). ESI-HRMS: m/z calcd for C12H16NaO5: 263.0890; found 263.0885.
<A NAME="RG40307ST-15">15</A>
Garber SB.
Kingsbury JS.
Gray BL.
Hoveyda AH.
J. Am. Chem. Soc.
2000,
122:
8168
<A NAME="RG40307ST-16">16</A>
Compound 9: [α]D
20 -11.5 (c 1.0, CHCl3). 1H NMR (C6D6): δ = 7.34 (d, J = 8.8 Hz, 2 H), 6.92 (d, J = 8.8 Hz, 2 H), 5.42 (s, 1 H), 4.52 (d, J = 11.0 Hz, 1 H), 4.34 (d, J = 11.0 Hz, 1 H), 4.27 (m, 1 H), 3.97 (d, J = 8.5 Hz, 1 H), 3.70 (d, J = 8.5 Hz, 1 H), 3.65 (m, 1 H), 3.44 (s, 3 H), 3.17 (br s, 1 H), 2.26-2.11 (m, 5 H),
2.03-1.94 (m, 3 H), 1.84 (m, 2 H), 1.66 (m, 1 H), 1.55 (s, 3 H), 1.52 (s, 3 H), 1.46
(s, 3 H), 1.45 (s, 3 H), 1.42 (s, 3 H), 0.98 (d, J = 6.7 Hz, 3 H). 13C NMR (C6D6): δ = 209.7 (Cq), 168.0 (Cq), 160.1 (Cq), 159.7 (Cq), 131.2 (Cq), 129.5 (CH), 114.1 (CH2), 108.6 (Cq), 106.3 (Cq), 96.1 (CH), 80.8 (Cq), 79.2 (CH), 75.9 (CH2), 70.6 (CH2), 64.9 (CH2), 54.8 (CH3), 48.4 (CH2), 41.5 (CH2), 40.7 (CH2), 40.2 (CH2), 34.1 (CH), 27.7 (CH3), 27.4 (CH3), 26.9 (CH2), 25.2 (CH3), 25.0 (CH3), 24.4 (CH3), 13.6 (CH3). ESI-HRMS: m/z calcd for C30H44NaO9: 571.2878; found: 571.2870.
<A NAME="RG40307ST-17">17</A>
Bode SE.
Wolberg M.
Müller M.
Synthesis
2006,
4:
557
<A NAME="RG40307ST-18">18</A>
Compound 2: [α]D
20 -21.8 (c 0.15, CHCl3). 1H NMR (C6D6): δ = 7.34 (d, J = 8.8, 2 H), 6.92 (d, J = 8.8 Hz, 2 H), 5.42 (s, 1 H), 4.52 (d, J = 11.0 Hz, 1 H), 4.34 (d, J = 11.0 Hz, 1 H), 4.28 (m, 1 H), 3.97 (d, J = 8.5 Hz, 1 H), 3.81 (d, J = 8.5 Hz, 1 H), 3.65 (m, 1 H), 3.44 (s, 3 H), 3.17 (br s, 1 H), 2.25-2.10 (m, 5 H),
2.03-1.90 (m, 3 H), 1.84 (m, 2 H), 1.67 (m, 1 H), 1.55 (s, 3 H), 1.52 (s, 3 H), 1.46
(s, 3 H), 1.45 (s, 3 H), 1.42 (s, 3 H), 0.98 (d, J = 6.7 Hz, 3 H). 13C NMR (C6D6): δ = 209.7 (Cq), 168.0 (Cq), 160.1 (Cq), 159.7 (Cq), 131.2 (Cq), 129.5 (CH), 114.1 (CH), 108.6 (Cq), 106.3 (Cq), 96.1 (CH), 80.8 (Cq), 79.2 (CH), 75.9 (CH2), 70.6 (CH2), 65.0 (CH), 54.8 (CH3), 48.4 (CH2), 41.5 (CH2), 40.7 (CH2), 40.2 (CH2), 34.1 (CH), 27.7 (CH3), 27.4 (CH3), 26.9 (CH2), 25.2 (CH3), 25.0 (CH3), 24.4 (CH3), 13.6 (CH3). ESI-HRMS: m/z calcd for C30H46NaO9: 573.3034; found: 573.3024.
