References
1
Daly JW.
Karle I.
Myers CW.
Tokuyama T.
Waters JA.
Witkop B.
Proc. Natl. Acad. Sci. U.S.A.
1971,
68:
1870
2
Takahashi K.
Witkop B.
Brossi A.
Maleque MA.
Albuquerque EX.
Helv. Chim. Acta
1982,
65:
252
3a For an overview on the synthesis of histrionicotoxin and related compounds, see: Kotera M.
Bull. Soc. Chim. Fr.
1989,
370
3b For recent syntheses of HTX see: Williams GM.
Roughley SD.
Davies JE.
Holmes AB.
J. Am. Chem. Soc.
1999,
121:
4900 ; and references cited therein
4a For recent approaches to the pHTX family see: Tanner D.
Hagberg L.
Poulsen A.
Tetrahedron
1999,
55:
1427
4b
Luzzio FA.
Fitch RW.
J. Org. Chem.
1999,
64:
5485
4c
Zhu J.
Royer J.
Quirion J.-C.
Husson H.-P.
Tetrahedron Lett.
1991,
32:
2485
4d
Compain P.
Gore J.
Vatele J.-M.
Tetrahedron Lett.
1995,
36:
4063
5a
Enders D.
Shilvock JP.
Chem. Soc. Rev.
2000,
29:
359
5b
Husson H.-P.
Royer J.
Chem. Soc. Rev.
1999,
28:
383
6a
Polniaszek RP.
Belmont SE.
J. Org. Chem.
1991,
56:
4868
6b
Enders D.
Gerdes P.
Kipphardt H.
Angew. Chem. Int. Ed. Engl.
1990,
2:
179
6c
Pierre F.
Enders D.
Tetrahedron Lett.
1999,
40:
5301
7a
Renaud T.
Hurvois JP.
Uriac P.
Eur. J. Org. Chem.
2001,
987
7b
Le Gall E.
Hurvois JP.
Sinbandhit S.
Eur. J. Org. Chem.
1999,
2645
8a
Harris M.
Grierson D.-S.
Husson H.-P.
Tetrahedron Lett.
1981,
22:
1511
8b
Zhu J.
Quirion J.-C.
Husson H.-P.
Tetrahedron Lett.
1989,
30:
6323
8c
Duhamel P.
Kotera M.
J. Org. Chem.
1982,
47:
1688
9a
Ziegler K.
Eberle H.
Ohlinger H.
Annalen
1933,
504:
94
9b
Fleming FF.
Shook BC.
Tetrahedron
2002,
58:
1
9c
Davis BR.
Garrat PJ. In
Comprehensive Organic Synthesis
Vol. 2:
Heathcock CH.
Pergamon;
Oxford:
1991.
p.795
10a
Diez A.
Castells J.
Forns P.
Rubiralta M.
Grierson DS.
Husson H.-P.
Solans X.
Font-Bardia M.
Tetrahedron
1994,
50:
6585
10b
Bonjoch J.
Quirante J.
Rodriguez M.
Bosch J.
Tetrahedron
1988,
44:
2087
11 For a review see: Albright JD.
Tetrahedron
1983,
39:
3207
12
Le Gall E.
Hurvois J.-P.
Renaud T.
Moinet C.
Tallec A.
Uriac P.
Sinbandhit S.
Toupet L.
Liebigs Ann. Recueil
1997,
2089
13 Crystallographic data for the structures 3d, 8-10 reported in this paper have been deposited at the Cambridge Crystallographic Data Center as supplementary publication no: 179964(3d), 179965(8), 179966(9), 179967(10). Copies of the data can be obtained free of charge on application to The Director CCDC, 12 Union Road, Cambridge CB2 IEZ, UK [fax: int. code+44(1221)336033, e-mail: deposit@ccdc.cam.ac.uk].
14a
Ciganek E.
Linn WJ.
Webster OW. In
The Chemistry of the Cyano Group
Rappoport Z.
Wiley;
New York:
1970.
p.589
14b
Arseniyadis S.
Kyler KS.
Watt DS.
Org. React.
1984,
31:
1
15
Kaneti J.
von Ragué Schleyer P.
Clark T.
Kos AJ.
Spitznagel GW.
Andrade JG.
Moffat JB.
J. Am. Chem. Soc.
1986,
108:
1481
16 For a review see: Boche G.
Angew. Chem. Int. Ed. Engl.
1989,
28:
277 ; and references cited therein
17
Enders D.
Kirshhoff J.
Gerdes P.
Mannes D.
Raabe G.
Runsink J.
Boche G.
Marsh M.
Ahlbrecht H.
Sommer H.
Eur. J. Org. Chem.
1998,
63
18
Bare TM.
Hershey ND.
House HO.
Swain CG.
J. Org. Chem.
1972,
37:
997
19
Mayer P.
Brunel P.
Chaplain C.
Piedecoq C.
Calmel F.
Schambel P.
Chopin P.
Wurch T.
Pauwels PJ.
Marien M.
Vidaluc J.-L.
Imbert T.
J. Med. Chem.
2000,
43:
3653
20
6: IR(neat) 2216, 2246 cm-1. 1H NMR (200 MHz, CDCl3): δ 1.35-1.90 (11 H, m), 2.00 (1 H, dm, J = 10.6 Hz), 2.15 (2 H, t, J = 6.5 Hz), 2.95 (1 H, dm, J = 12.0 Hz), 3.12 (1 H, tm, J = 12.0 Hz), 7.15-7.35 (5 H, m).
[13]
C NMR (50 MHz, CDCl3): δ 17.34, 22.25, 23.16, 25.69, 26.20, 36.03, 38.13, 53.35, 61.52, 119.81, 120.64, 127.03, 127.52, 129.58, 149.35. C17H21N3: calcd 267.1736, found 267.1737 (MS). C17H21N3: calcd. C 76.37, H 7.92, N 15.72; found C 76.11, H 8.02, N 15.56.
21a
Toro A.
Nowak P.
Deslongchamps P.
J. Am. Chem. Soc.
2000,
122:
4526
21b
Dansou B.
Pichon C.
Dhal R.
Brown E.
Mille S.
Eur. J. Org. Chem.
2000,
1527
21c
Linders JTM.
Flippen-Anderson JL.
George CF.
Rice KC.
Tetrahedron Lett.
1999,
40:
3905
21d
Luyten M.
Keese R.
Tetrahedron
1986,
42:
1687
22
Piers E.
Abeysekara BF.
Herbert DJ.
Suckling ID.
J. Chem. Soc., Chem. Commun.
1982,
404
23
Takaya H.
Naota T.
Murahashi S.-I.
J. Am. Chem. Soc.
1998,
120:
4244
24
Curran DP.
Liu W.
Synlett
1999,
117
25 A solution (20 mL, THF) of 6 (0.5 g, 1.87 mmol) was cooled to -30 °C and treated dropwise (by syringe) with a 2 M solution of LDA (0.94 mL, 1.87 mmol). The solution was allowed to warm to -20 °C and maintained at that temperature for 1 h, before being stirred at r.t. for 3 h. The reaction mixture was quenched with water and extracted with CH2Cl2. The organic phases were combined, dried over MgSO4, and concentrated in vacuo. The crude material was purified over a silica column (diethyl ether-petroleum ether, 1:1) to afford 8 (0.433 g, 87%).