References
1a
De Boer C.
Meulman PA.
Wnuk RJ.
Peterson DH.
J. Antibiot.
1970,
23:
442
1b
Sasaki K.
Rinehart KJ.
Slomp G.
Grostic MF.
Olson EC.
J. Am. Chem. Soc.
1970,
92:
7591
Recent reviews:
2a
Maloney A.
Workman P.
Exp. Opin. Biol. Ther.
2002,
2:
3
2b
Piper PW.
Curr. Opin. Invest. Drugs
2001,
2:
1606
2c
Ochel H.-J.
Eichhorh K.
Gademann G.
Cell
Stress Chaperones
2001,
6:
105
2d
Neckers LM.
Schulte TW.
Mimnaugh E.
Invest. New Drugs
1999,
17:
361
3
Holstein I.
Robertson D.
Di Stefano F.
Workman P.
Clarke PA.
Cancer
Res.
2001,
61:
4003 ;
and references cited therein
4a
Whitesell L.
Shifrin SD.
Schwab G.
Neckers LM.
Cancer
Res.
1992,
52:
1721
4b
Whitesell L.
Mimnaugh EG.
De Costa B.
Myers CE.
Neckers LM.
Proc. Natl. Acad. Sci. U.S.A.
1994,
91:
8324
4c
Stebbins CE.
Russo AA.
Schneider C.
Rosen N.
Hartl FU.
Pavletich NP.
Cell
1997,
89:
239
Reviews on Hsp90:
5a
Richter K.
Buchner J.
J. Cell. Phys.
2001,
188:
281
5b
Buchner J.
Trends
Biochem. Sci.
1999,
24:
136
6a
Dolinski KJ.
Cardenas ME.
Heitman J.
Mol. Cell Biol.
1998,
18:
7344
6b
Webb CP.
Hose CD.
Koochekpour S.
Jeffers M.
Oskarsson M.
Suasville E.
Monks A.
Vande Wourde GF.
Cancer
Res.
2000,
60:
342
7
Schill G.
Merkel C.
Zürchner C.
Liebigs
Ann. Chem.
1977,
288
8
Andrus MB.
Meredith EL.
Soma Sekhar BBV.
Org. Lett.
2001,
3:
259
9a
Baker R.
Castro JL.
J.
Chem. Soc., Perkin Trans. 1
1990,
47
9b
Evans DA.
Miller SJ.
Ennis MD.
J. Org. Chem.
1993,
58:
471
9c
Panek JS.
Xu F.
Rondón AC.
J. Am. Chem. Soc.
1998,
120:
4113
9d Formal syntheses: Coutts SJ.
Kallmerten J.
Tetrahedron
Lett.
1990,
31:
4301
9e See also: Martin SF.
Dodge JA.
Burgess LE.
Limberakis C.
Hartmann M.
Tetrahedron
1996,
52:
3229
10
Nakat M.
Osumi T.
Ueno A.
Kimura T.
Tamai T.
Tatsuta K.
Bull. Chem. Soc. Jpn.
1992,
65:
2974
Recent Reviews:
11a
Trnka TM.
Grubbs RH.
Acc.
Chem. Res.
2001,
34:
18
11b
Fürstner A.
Angew. Chem. Int. Ed.
2000,
39:
3012
11c
Maier ME.
Angew. Chem. Int. Ed.
2000,
39:
2073
11d
Grubbs RH.
Chang S.
Tetrahedron
1998,
54:
4413
11e
Schuster M.
Blechert S.
Angew. Chem., Int. Ed. Engl.
1997,
36:
2036
Examples for the use of 1,3-dienes
as substrates in ring closing metathesis reactions:
12a
Kirkland TA.
Grubbs RH.
J.
Org. Chem.
1997,
62:
7310
12b
Dvorak CA.
Schmitz WD.
Poon DJ.
Pryde DC.
Lawson JP.
Amos RA.
Meyers AI.
Angew. Chem. Int.
Ed.
2000,
39:
1664
12c
Benningshof JCJ.
Blaauw RH.
van Ginkel AE.
Rutjes FPJT.
Fraanje J.
Goubitz K.
Schenk H.
Hiemstra H.
Chem. Commun.
2000,
1465
12d
Wagner J.
Cabrejas LMM.
Grossmith CE.
Papageorgiou C.
Senia F.
Wagner D.
France J.
Nolan SP.
J.
Org. Chem.
2000,
65:
9255
12e
Snider BB.
Hawryluk NA.
Org.
Lett.
2001,
3:
569
12f
Garbaccio RM.
Stachel SJ.
Baeschlin DK.
Danishefsky SJ.
J.
Am. Chem. Soc.
2001,
123:
10903
Examples for the use of vinyl benzoic
acid derivatives in ring closing metathesis reactions:
13a
Fürstner A.
Thiel OR.
Kindler N.
Bartkowska B.
J. Org.
Chem.
2000,
65:
7990
13b
Barrett AGM.
Hamprecht D.
James RA.
Ohkubo M.
Procopiou PA.
Toledo MA.
White AJP.
Williams DJ.
J. Org. Chem.
2001,
66:
2187
14a
Carpino LA.
J. Am. Chem. Soc.
1993,
115:
4397
14b
Carpino LA.
El-Faham A.
J. Org.
Chem.
1994,
59:
697
14c
Humphrey JM.
Chamberlain AR.
Chem.
Rev.
1997,
97:
2243
15a
House HO.
Rasmusson GR.
J. Org. Chem.
1961,
26:
4278
15b
Piers E.
Jung GL.
Ruediger EH.
Can. J. Chem.
1987,
65:
670
15c
Elemes Y.
Foote CS.
J. Am. Chem. Soc.
1992,
114:
6044
16
Schwab P.
Grubbs RH.
Ziller JW.
J. Am. Chem. Soc.
1996,
118:
100
17a
Huang J.
Stevens ED.
Nolan SP.
Petersen JL.
J. Am. Chem. Soc.
1999,
121:
2674
17b
Scholl M.
Trnka TM.
Morgan JP.
Grubbs RH.
Tetrahedron
Lett.
1999,
40:
2247
17c
Ackermann L.
Fürstner A.
Weskamp T.
Kohl FJ.
Herrmann WA.
Tetrahedron Lett.
1999,
40:
4787
17d
Weskamp T.
Kohl FJ.
Hieringer W.
Gleich D.
Herrmann WA.
Angew.
Chem. Int. Ed.
1999,
38:
2416
18a
Fürstner A.
Langemann K.
J.
Am. Chem. Soc.
1997,
119:
9130
18b
Baba Y.
Saha G.
Nakao S.
Iwata C.
Tanaka T.
Ibuka T.
Ohishi H.
Takemoto Y.
J.
Org. Chem.
2001,
66:
81
19 Representative procedure for the ring
closing metathesis 8 → 10: A solution of anilide (8d,
50 mg, 113 µmol) in 5 mL of dichloromethane was slowly
added to a refluxing solution of Grubbs’s catalyst (9a, 8.6 mg, 11.3 µmol) in 220
mL of dichloromethane. After 36 h at reflux, the reaction mixture was
cooled and the solvent was removed in vacuo. The residue was purified
by flash chromatography (pentane/EtOAc = 9:1).
Compound 10d (36 mg, 87 µmol,
77%) was obtained as a colorless liquid. 1H
NMR (360 MHz, CDCl3): δ = 1.10-1.47
(m, 2 H), 1.65-1.68 (m, 2 H), 2.04 (d, J = 0.7 Hz,
3 H), 2.21 (virt. q, J ≅ 8.0
Hz, 2 H), 2.70 (t, J = 6.5
Hz, 2 H), 3.67 (s, 3 H), 3.81 (s, 3 H), 3.87 (s, 3 H), 5.96 (virt.
q, J ≅ 9.1 Hz, 1 H), 6.32 (virt.
t, J ≅ 10.9 Hz, 1 H), 6.99 (d, J = 11.3 Hz,
1 H), 7.95 (s, 1 H), 8.23 (s br, 1 H). 13C
NMR (90 MHz, CDCl3): δ = 12.6,
22.4, 27.2, 27.4, 28.1, 28.5, 28.6, 28.8, 29.4, 29.6, 29.7, 55.9,
60.9, 61.3, 101.4, 124.1, 126.7, 127.6, 128.8, 133.5, 137.9, 141.2,
143.3, 149.4, 168.4.