References and Notes
For recent examples, see:
<A NAME="RD29309ST-1A">1a</A>
Rigano D.
Grassia A.
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54:
2111
<A NAME="RD29309ST-1C">1c</A>
Jones WP.
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Cordell GA.
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70:
372
<A NAME="RD29309ST-1D">1d</A>
Ueoka R.
Nakao Y.
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Matsunaga S.
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71:
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For recent applications of butenolides
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<A NAME="RD29309ST-2A">2a</A>
Doroh B.
Sulikowski GA.
Org. Lett.
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903
<A NAME="RD29309ST-2B">2b</A>
Tang B.
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<A NAME="RD29309ST-2C">2c</A>
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<A NAME="RD29309ST-2D">2d</A>
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<A NAME="RD29309ST-3A">3a</A>
Rao
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<A NAME="RD29309ST-3B">3b</A>
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<A NAME="RD29309ST-5A">5a</A>
Caine D.
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<A NAME="RD29309ST-5B">5b</A> For a later racemic synthesis
of 1, see:
Bonete P.
Nájera C.
J. Org. Chem.
1994,
59:
3202
For syntheses of (+)-1 and/or (-)-1, see:
<A NAME="RD29309ST-6A">6a</A>
Ortuño RM.
Bigorra J.
Font J.
Tetrahedron
1987,
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<A NAME="RD29309ST-6B">6b</A>
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Okumura Y.
Itai J.
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1537
<A NAME="RD29309ST-6C">6c</A>
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113:
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<A NAME="RD29309ST-6D">6d</A>
Gibson CL.
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7:
1281
<A NAME="RD29309ST-6E">6e</A>
Ha H.-J.
Yoon K.-N.
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Park Y.-S.
Lim M.-S.
Yim Y.-G.
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63:
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Liu HW.
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<A NAME="RD29309ST-6G">6g</A>
Liu H.
Zhang T.
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2006,
18:
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<A NAME="RD29309ST-6H">6h</A>
Kamal A.
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<A NAME="RD29309ST-7">7</A>
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68:
465
For recent, or related, syntheses
of the butenolide structure, see:
<A NAME="RD29309ST-8A">8a</A>
Mulzer J.
Pietschmann C.
Schöllhorn B.
Buschmann J.
Luger P.
Liebigs
Ann.
1995,
1433
<A NAME="RD29309ST-8B">8b</A>
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<A NAME="RD29309ST-9">9</A>
Kabeya M.
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<A NAME="RD29309ST-10">10</A> For a related preparation of 8, see:
White JD.
Quaranta L.
Wang G.
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Org. Chem.
2007,
72:
1717
<A NAME="RD29309ST-11A">11a</A>
Baer E.
Fischer HOL.
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<A NAME="RD29309ST-11B">11b</A>
LeCocq J.
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<A NAME="RD29309ST-11C">11c</A> For a review, see:
Jurczak J.
Pikul S.
Bauer T.
Tetrahedron
1986,
42:
447
<A NAME="RD29309ST-11D">11d</A> For other recent methods for
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Zhong Y.-L.
Shing TKM.
J. Org. Chem.
1997,
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<A NAME="RD29309ST-11E">11e</A>
Palomo C.
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<A NAME="RD29309ST-12A">12a</A>
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Kuster BFM.
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1991,
2:
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Ruholl H.
Schäfer HJ.
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1988,
54
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Tanner D.
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<A NAME="RD29309ST-14">14</A> For a similar strategy, see:
Tomioka K.
Tanaka M.
Koga K.
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1989,
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1201
<A NAME="RD29309ST-15A">15a</A>
Jacobi PA.
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5475
<A NAME="RD29309ST-15B">15b</A>
Munier P.
Krusinski A.
Picq D.
Anker D.
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1995,
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1229
<A NAME="RD29309ST-15C">15c</A>
Kis K.
Wungsintaweekul J.
Eisenreich W.
Zenk MH.
Bacher A.
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Scholte AA.
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<A NAME="RD29309ST-16">16</A>
Full experimental details for the
compounds 2, 18, 23 and (S)-(-)-1, including proton and carbon NMR spectra,
are available in the Supporting Information. The following spectroscopic
data were recorded for key intermediates.
1-[(
R
)-2,2-Dimethyl-1,3-dioxolan-4-yl]-4-(4-methoxy-benzyloxy)butan-1-one (5). [α]D
²0 +1.6
(c 1.2 in CHCl3); IR(film):
2988, 2935, 2860, 1716, 1612, 1513, 1456, 1373, 1302, 1210 cm-¹; ¹H
NMR (300 MHz, CDCl3): δ = 7.25-7.22
(m, 2 H, ArH), 6.89-6.83 (m, 2 H, ArH),
4.40 (s, 2 H, OCH2PMP), 4.23 (dd, J = 7.7, 5.7 Hz, 1 H,
OCHHCH), 4.17 (dd, J = 8.7,
8.0 Hz, 1 H, CH), 3.95 (dd, J = 8.7,
5.7 Hz, 1 H, OCHHCH), 3.80 (s,
3 H, OCH3), 3.45 (t, J = 6.2
Hz, 2 H, PMBOCH2), 2.70 (t, J = 7.2
Hz, 2 H, COCH2), 1.92-1.83 (m, 2 H,
PMBOCH2CH
2), 1.47
(d, J = 0.6 Hz, 3 H,
CH3), 1.38 (d, J = 0.6
Hz, 3 H, CH3); ¹³C
NMR (75 MHz, CDCl3): δ = 210.4, 159.1,
130.4, 129.2, 113.7, 110.8, 80.2, 72.5, 68.8, 66.5, 55.2, 35.4,
26.0, 25.0, 23.1; HRMS (EI): m/z [M]+ calcd
for C17H24O5: 308.1624; found:
308.1647 (5%).
1-[(
R
)-2,2-Dimethyl-1,3-dioxolan-4-yl]pent-4-en-1-one (9). [α]D
²0 +14.9
(c 1.0 in CHCl3); IR(film):
3079, 2988, 2934, 1716, 1641, 1373, 1217, 1068 cm-¹; ¹H
NMR (300 MHz, CDCl3): δ = 5.82 (ddt, J = 16.8, 10.4, 6.4 Hz, 1 H, H2C=CH), 5.08-4.95 (m, 2 H,
C=CH2), 4.43 (dd, J = 5.5,
2.3 Hz, 1 H, OCHH), 4.19 (t, J = 7.7 Hz, 1 H, CH),
3.98 (dd,
J = 5.5,
2.3 Hz, 1 H, OCHH), 2.74-2.68
(m, 2 H, COCH2), 2.37-2.29 (m, 2 H,
H2C=CHCH
2),
1.48 (s, 3 H, CH3), 1.39 (s, 3 H, CH3); ¹³C
NMR (75 MHz, CDCl3): δ = 210.1, 136.9, 115.3,
110.9, 80.2, 66.5, 37.7, 26.9, 26.0, 25.0.
4-(
tert
-Butyldimethylsilanyloxy)-1-[(
R
)-2,2-dimethyl-1,3-dioxolan-4-yl]butan-1-one (10). [α]D
²0 -0.4
(c 1.1 in CHCl3); IR(film):
2932, 2859, 1718, 1255, 1101 cm-¹; ¹H NMR
(300 MHz, CDCl3): δ = 4.44 (dd, J = 7.7, 5.6 Hz, 1 H, OCHH), 4.19 (dd, J = 8.7,
7.7 Hz, 1 H, CH), 3.98 (dd,
J = 8.7,
5.7 Hz, 1 H, OCHH), 3.62 (t, J = 6.0 Hz, 2 H, TBSOCH2),
2.69 (t, J = 7.0 Hz, 2 H,
COCH2), 1.83-1.74 (m, 2 H, TBSOCH2CH
2), 1.48 (s, 3 H,
CH3), 1.39 (s, 3 H, CH3), 0.88 (s,
9 H, Si(CH3)3), 0.03 (s, 6 H,
Si(CH3)2); ¹³C
NMR (75 MHz, CDCl3): δ = 210.8, 110.9,
80.3, 66.5, 62.0, 35.0, 26.0, 25.9, 25.0, 18.3, -5.4; HRMS
(ES): m/z [M + Na]+ calcd
for C15H30O4SiNa: 325.1811; found:
325.1834 (20%).
tert
-Butyl-{4-[(
S
)-2,2-dimethyl-1,3-dioxolan-4-yl]pent-4-enyloxy}dimethylsilane (11). [α]D
²0 +6.0
(c 0.9 in CHCl3); IR(film):
2928, 2857, 1650, 1471, 1379, 1256, 1214 cm-¹; ¹H
NMR (300 MHz, CDCl3): δ = 5.15 (br
s, 1 H, C=CHH), 4.90
(t, J = 0.7 Hz, 1 H,
C=CHH), 4.53 (t, J = 7.5 Hz, 1 H, OCHH), 4.11 (dd, J = 8.0,
6.5 Hz, 1 H, CH), 3.65-3.58 (m, 3 H,
OCHH and TBSOCH2), 2.13-1.97
(m, 2 H, H2C=CCH
2),
1.74-1.64
(m, 2 H, TBSOCH2CH
2),
1.44 (m, 3 H, CH3), 1.40 (s, 3 H, CH3),
0.89 (s, 9 H, Si(CH3)3), 0.04 (s,
6 H, Si(CH3)2); ¹³C
NMR (75 MHz, CDCl3): δ = 146.7, 111.1, 109.6,
79.4, 69.4, 63.1, 31.5, 28.1, 26.8, 26.3, 26.1, 18.7,
-4.9.
<A NAME="RD29309ST-17">17</A>
Karioti A.
Skaltsa H.
Linden A.
Perozzo R.
Brun R.
Tasdemir D.
J. Org. Chem.
2007,
72:
8103
