References and Notes
<A NAME="RD18708ST-1">1</A>
Current address: L. J. Montgomery,
Peakdale Molecular Ltd., Peakdale Science Park, Sheffield Road,
Chapel-en-le-Frith, High Peak SK23 OPG, U.K.
<A NAME="RD18708ST-2">2</A>
Tsunakawa M.
Tenmyo O.
Tomita K.
Naruse N.
Kotake C.
Miyaki T.
Konishi M.
Oki T.
J. Antibiot.
1992,
45:
180
<A NAME="RD18708ST-3A">3a</A>
Keller-Schierlein W.
Muntwyler R.
Pache W.
Zaehner H.
Helv.
Chim. Acta
1969,
52:
127
<A NAME="RD18708ST-3B">3b</A>
Muntwyler R.
Keller-Schierlein W.
Helv. Chim. Acta
1972,
55:
2071
<A NAME="RD18708ST-3C">3c</A>
Brufani M.
Cerrini S.
Fedeli W.
Mazza F.
Muntwyler R.
Helv.
Chim. Acta
1972,
55:
2094
<A NAME="RD18708ST-4A">4a</A>
Mallams AK.
Puar MS.
Rossman RR.
J.
Am. Chem. Soc.
1981,
103:
3938
<A NAME="RD18708ST-4B">4b</A>
Mallams AK.
Puar MS.
Rossman RR.
McPhail AT.
Macfarlane RD.
J. Am. Chem. Soc.
1981,
103:
3940
<A NAME="RD18708ST-4C">4c</A>
Waitz JA.
Horan AC.
Kalyanpur M.
Lee BK.
Loebenberg D.
Marquez JA.
Miller G.
Patel MG.
J.
Antibiot.
1981,
34:
1101
<A NAME="RD18708ST-4D">4d</A>
Mallams AK.
Puar MS.
Rossman RR.
McPhail AT.
Macfarlane RD.
Stephens RL.
J. Chem. Soc., Perkin Trans. 1
1983,
1497
<A NAME="RD18708ST-5">5</A>
Kusumi T.
Ichikawa A.
Kakisawa H.
Tsunakawa M.
Konishi M.
Oki T.
J. Am. Chem. Soc.
1991,
113:
8947
<A NAME="RD18708ST-6A">6a</A>
Roush WR.
Barda DA.
Org.
Lett.
2002,
4:
1539
<A NAME="RD18708ST-6B">6b</A>
Roush WR.
Barda DA.
Limberakis C.
Kunz RK.
Tetrahedron
2002,
58:
6433
<A NAME="RD18708ST-7A">7a</A>
Roush WR.
Limberakis C.
Kunz RK.
Barda DA.
Org.
Lett.
2002,
4:
1543
<A NAME="RD18708ST-7B">7b</A>
Bedel O.
Franxais A.
Haudrechy Y.
Synlett
2005,
2313
<A NAME="RD18708ST-7C">7c</A>
Trullinger TK.
Qi J.
Roush WR.
J. Org. Chem.
2006,
71:
6915
<A NAME="RD18708ST-8">8</A>
Jia X.-Y.
Tian Z.-H.
Shao L.
Qu X.-D.
Zhao Q.-F.
Tang J.
Tang G.-L.
Liu W.
Chem.
Biol.
2006,
13:
575
<A NAME="RD18708ST-9">9</A>
Zhang H.
White-Phillip JA.
Melancon CE.
Kwon H.-J.
Yu W.-L.
Liu H.-W.
J
Am. Chem. Soc.
2007,
129:
14670
<A NAME="RD18708ST-10A">10a</A>
Sun Y.
Hong H.
Gillies F.
Spencer JB.
Leadlay PF.
ChemBioChem.
2008,
9:
150
<A NAME="RD18708ST-10B">10b</A>
Demydchuk Y.
Sun Y.
Hong H.
Staunton J.
Spencer JB.
Leadlay PF.
ChemBioChem.
2008,
9:
1136
<A NAME="RD18708ST-11">11</A>
Oikawa H.
Tokiwano T.
Nat. Prod. Rep.
2004,
21:
321
For recent examples, see:
<A NAME="RD18708ST-12A">12a</A>
Dixon DJ.
Ley SV.
Gracza T.
Szolcsanyi P.
J. Chem.
Soc., Perkin Trans. 1
1999,
839
<A NAME="RD18708ST-12B">12b</A>
Dixon DJ.
Ley SV.
Longbottom DA.
J. Chem. Soc., Perkin Trans. 1
1999,
2231
<A NAME="RD18708ST-12C">12c</A>
Sodeoka M.
Sampe R.
Kojima S.
Baba Y.
Usui T.
Ueda K.
Osada H.
J. Med. Chem.
2001,
44:
3216
For examples, see:
<A NAME="RD18708ST-13A">13a</A>
Takeda K.
Yano S.
Yoshii E.
Tetrahedron
Lett.
1988,
29:
6951
<A NAME="RD18708ST-13B">13b</A>
Takeda K.
Kawanishi E.
Nakamura H.
Yoshii E.
Tetrahedron Lett.
1991,
32:
4925
<A NAME="RD18708ST-13C">13c</A>
Snider BB.
Zou Y.
Org. Lett.
2005,
7:
4939
<A NAME="RD18708ST-13D">13d</A>
Zapf CW.
Harrison BA.
Drahl C.
Sorensen EJ.
Angew.
Chem. Int. Ed.
2005,
44:
6533
<A NAME="RD18708ST-13E">13e</A>
Couladouros EA.
Bouzas EA.
Magos AD.
Tetrahedron
2006,
62:
5272
<A NAME="RD18708ST-13F">13f</A>
Nicolaou KC.
Harrison ST.
J.
Am. Chem. Soc.
2007,
129:
429
<A NAME="RD18708ST-14A">14a</A>
Takeda K.
Yano S.
Sato M.
Yoshii E.
J. Org. Chem.
1987,
52:
4135
<A NAME="RD18708ST-14B">14b</A>
Paintner FF.
Bauschke G.
Kestel M.
Tetrahedron Lett.
2000,
41:
9977
<A NAME="RD18708ST-15">15</A>
Pelter A.
Al-Bayati RIH.
Ayoub MT.
Lewis W.
Pardasani P.
Hänsel R.
J. Chem. Soc., Perkin Trans.
1
1987,
717
<A NAME="RD18708ST-16">16</A>
Wei X.
Taylor RJK.
Tetrahedron Lett.
1998,
39:
3815
<A NAME="RD18708ST-17">17</A>
General Procedure
for the Acylation of Compounds 18 and 28: To a stirred solution
of 2,2,6,6-tetramethyl-piperidine (TMP, 0.84 mL, 5.00 mmol) in THF
(5.50 mL) at -78 ˚C under argon was added n-BuLi (1.60 M in hexanes, 3.70 mL, 5.92
mmol) dropwise. After 15 min the solution was warmed to r.t. and
stirred for a further 30 min to give a 0.5 M solution of LTMP. To
a stirred solution of 18 or 28 (1.4
mmol) in THF (20 mL) at -78 ˚C under argon was added
a solution of LTMP (0.5 M in THF, 4.40 mL, 2.20 mmol) dropwise.
After stirring for 1 h, a solution of ester (0.70 mmol) in THF (2
mL) was added dropwise. The reaction mixture was stirred at -78 ˚C
for 24 h and quenched with sat. citric acid (20 mL). The organic
layer was separated, and the aqueous layer was extracted with CH2Cl2 (5 × 50
mL). The combined organic layers were dried with MgSO4 and
the solvent was removed in vacuo.
Purification
and Characterization of Compound 29: Purification by flash
column chromatography (hexane-EtOAc, 5:1) yielded the product
as a yellow oil. ¹H NMR (400 MHz, CDCl3): δ = 1.34
(t, J = 7.0 Hz, 3 H), 1.74 (d, J = 7.0 Hz,
3 H), 1.83 (s, 3 H), 1.99 (s, 3 H), 2.02 (s, 3 H), 4.14 (q, J = 7.0 Hz, 2 H), 5.13 (d, J = 1.0 Hz, 1 H), 5.17 (d, J = 1.0 Hz, 1 H), 5.61 (q, J = 7.0 Hz, 1 H), 6.16 (s, 1
H), 6.55 (dd, J = 11.0, 15.0
Hz, 1 H), 6.67 (d, J = 15.0
Hz, 1 H), 7.04 (d, J = 11.0
Hz, 1 H). ¹³C NMR (175 MHz, CDCl3): δ = 11.6, 14.0,
14.2, 14.9, 16.6, 70.1, 93.9, 104.8, 122.4, 129.6, 132.6, 134.0,
135.4, 142.4, 146.9, 149.4 149.5, 164.4, 166.6, 190.6. IR(film):
2921, 1768, 1667 cm-¹. HRMS (ESI): m/z calcd
for C20H24O4Na+:
351.1561; found: 351.1573.
