RSS-Feed abonnieren
DOI: 10.1055/s-2008-1078266
Convergent Synthesis of the A-J Ring System of Yessotoxin
Publikationsverlauf
Publikationsdatum:
21. August 2008 (online)
![](https://www.thieme-connect.de/media/synlett/200815/lookinside/thumbnails/10.1055-s-2008-1078266-1.jpg)
Abstract
A highly convergent synthesis of the A-J ring system of yessotoxin was achieved. A convergent strategy via α-cyano ethers was extensively applied in the assembly of the F and IJ ring fragments to afford the FGHIJ ring unit, followed by coupling with the ABC ring unit.
Key words
polyether - convergent synthesis - α-cyano ether - ring-closing metathesis - reductive etherification
-
1a
Murata M.Kumagai M.Lee JS.Yasumoto T. Tetrahedron Lett. 1987, 28: 5869 -
1b
Satake M.Terasawa K.Kadowaki Y.Yasumoto T. Tetrahedron Lett. 1996, 37: 5955 -
1c
Takahashi H.Kusumi T.Kan Y.Satake M.Yasumoto T. Tetrahedron Lett. 1996, 37: 7087 - 2
Paz B.Riobó P.Fernández ML.Fraga S.Franco JM. Toxicon 2004, 44: 251 -
3a
Aune T.Sørby R.Yasumoto T.Ramstad H.Landsverk T. Toxicon 2002, 40: 77 -
3b
Tubaro A.Sosa S.Alitinier G.Soranzo MR.Satake M.Loggia RD.Yasumoto T. Toxicon 2004, 43: 439 - 4
Terao K.Ito E.Oarada M.Murata M.Yasumoto T. Toxicon 1990, 28: 1095 - 5
de la Rosa LA.Alfonso A.Vilariño N.Vieytes MR.Botana LM. Biochem. Pharmacol. 2001, 61: 827 - 6
Alfonso A.de la Rosa L.Vieytes MR.Yasumoto T.Botana LM. Biochem. Pharmacol. 2003, 65: 193 - 7
Korsnes MS.Hetland DL.Espenes A.Aune T. Toxicol. in Vitro 2006, 20: 1419 -
8a
Ciminiello P.Fattorusso E.Forino M.Magno S.Poletti R.Viviani R. Tetrahedron Lett. 1998, 39: 8897 -
8b
Suzuki T.Horie Y.Koike K.Satake M.Oshima Y.Iwataki M.Yoshimatsu S. J. Chromatogr. A 2007, 1142: 172 - Synthetic studies of yessotoxin and its analogues, see:
-
9a
Suzuki K.Nakata T. Org. Lett. 2002, 4: 3943 -
9b
Suzuki K.Nakata T. Org. Lett. 2002, 4: 2739 -
9c
Mori Y.Nogami K.Hayashi H.Noyori R. J. Org. Chem. 2003, 68: 9050 -
9d
Mori Y.Takase T.Noyori R. Tetrahedron Lett. 2003, 44: 2319 -
9e
Mori Y.Hayashi H. Tetrahedron 2002, 58: 1789 -
9f
Furuta H.Hase M.Noyori R.Mori Y. Tetrahedron 2005, 61: 8589 -
9g
Kadota I.Ueno H.Yamamoto Y. Tetrahedron Lett. 2003, 44: 8935 -
9h
Kadota I.Ueno H.Sato Y.Yamamoto Y. Tetrahedron Lett. 2006, 47: 89 -
9i
Trost BM.Rhee YH. Org. Lett. 2004, 6: 4311 - Reviews on the total synthesis of ladder-shaped polyethers, see:
-
10a
Nakata T. Chem. Rev. 2005, 105: 4314 -
10b
Inoue M. Chem. Rev. 2005, 105: 4379 -
10c
Kadota I.Yamamoto Y. Acc. Chem. Res. 2005, 38: 423 -
10d
Sasaki M.Fuwa H. Synlett 2004, 1851 -
10e
Inoue M. Org. Biomol. Chem. 2004, 2: 1811 -
10f
Marmsäter FP.West FG. Chem. Eur. J. 2002, 8: 4346 -
10g
Evans PA.Delouvrie B. Curr. Opin. Drug Discovery Dev. 2002, 5: 986 -
10h
Mori Y. Chem. Eur. J. 1997, 3: 849 -
10i
Alvarez E.Candenas M.-L.Pérez R.Ravelo JL.Martín JD. Chem. Rev. 1995, 95: 1953 -
11a
Oishi T.Watanabe K.Murata M. Tetrahedron Lett. 2003, 44: 7315 -
11b
Watanabe K.Suzuki M.Murata M.Oishi T. Tetrahedron Lett. 2005, 46: 3991 -
11c
Oishi T.Suzuki M.Watanabe K.Murata M. Heterocycles 2006, 69: 91 -
Oishi T.Suzuki M.Watanabe K.Murata M. Tetrahedron Lett. 2006, 47: 3975 -
11d
Watanabe K.Minato H.Murata M.Oishi T. Heterocycles 2007, 72: 207 -
12a
Fukuzawa S.-I.Tsuchimoto T.Hotaka T.Hiyama T. Synlett 1995, 1077 -
12b
Ishihara K.Karumi Y.Kubota M.Yamamoto H. Synlett 1996, 839 -
12c
Inoue M.Sasaki M.Tachibana K. Angew. Chem. Int. Ed. 1998, 37: 965 -
14a
Dess DB.Martin JC. J. Org. Chem. 1983, 48: 4155 -
14b
Ireland RE.Liu L. J. Org. Chem. 1993, 58: 2899 -
15a
Fu GC.Nguyen ST.Grubbs RH. J. Am. Chem. Soc. 1993, 115: 9856 -
15b
Fu GC.Nguyen ST.Grubbs RH. Angew. Chem., Int. Ed. Engl. 1995, 34: 2039 - 16
Scholl M.Ding S.Lee CW.Grubbs RH. Org. Lett. 1999, 1: 953 -
17a
Lewis MD.Cha JK.Kishi Y. J. Am. Chem. Soc. 1982, 104: 4976 -
17b
Nicolaou KC.Hwang C.-K.Nugiel DA. J. Am. Chem. Soc. 1989, 111: 4136 -
17c
Oishi T.Nagumo Y.Shoji M.Le Brazidec J.-Y.Uehara H.Hirama M. Chem. Commun. 1999, 2035 - 18
Hatakeyama S.Mori H.Kitano K.Yamada H.Nishizawa M. Tetrahedron Lett. 1994, 35: 4367 -
19a
Nicolaou KC.Prasad CVC.Hwang C.-K.Duggan ME.Veale CA. J. Am. Chem. Soc. 1989, 111: 5321 -
19b
Tsukano C.Sasaki M. J. Am. Chem. Soc. 2003, 125: 14294 - 20
Grieco PA.Gilman S.Nishizawa M. J. Org. Chem. 1976, 41: 1485 -
21a
Gaunt MJ.Yu J.Spencer JB. J. Org. Chem. 1998, 63: 4172 -
21b
Xia J.Abbas SA.Locke RD.Piskorz CF.Alderfer JL.Matta KL. Tetrahedron Lett. 2000, 41: 169
References and Notes
The carbon numbering of compounds in this paper corresponds to that of YTX.
22
Physical Data
of 2
[α]D
³0 -10.8
(c 0.04, CHCl3). ¹H
NMR (500 MHz, C6D6): δ = 7.30-6.99
(10 H, m, Ph), 4.41 (1 H, d, J = 12.0
Hz, Bn), 4.37 (1 H, d, J = 12.0
Hz, Bn), 4.33 (1 H, d, J = 12.0
Hz, Bn), 4.18 (1 H, d, J = 12.0
Hz, Bn), 4.00 (1 H, d, J = 2.5
Hz, H32), 3.88 (1 H, ddd, J = 11.5,
10.0, 4.5 Hz, H30), 3.82 (1 H, dd, J = 13.5,
4.0 Hz, H34), 3.72 (1 H, m, H37), 3.65 (1 H, dd, J = 11.0,
4.0 Hz, H38), 3.60 (1 H, dd, J = 11.0,
2.0 Hz, H38), 3.49 (4 H, m, H1, H1, H4, H36), 3.31 (1 H, ddd, J = 10.5, 9.5,
4.0 Hz, H15), 3.27-3.19 (3 H, m, H7, H20, H22), 3.15 (1
H, ddd, J = 9.5,
9.0, 5.5 Hz, H16), 3.12-3.07 (2 H, m, H13, H28), 3.05-3.00
(3 H, m, H9, H10, H31), 2.94-2.88 (2 H, m, H6, H12), 2.64
(1 H, dd, J = 9.5,
9.0 Hz, H27), 2.59 (1 H, ddd, J = 12.0,
4.5, 4.0 Hz, H14), 2.52 (1 H, ddd, J = 10.5, 4.5,
4.0 Hz, H11), 2.42 (1 H, ddd, J = 10.5,
4.5, 4.0 Hz, H29), 2.36-2.29 (2 H, m, H8, H35), 2.20 (1
H, ddd, J = 10.5, 4.0,
4.0 Hz, H5), 2.05-1.98 (2 H, m, H17, H17), 1.91-1.81 (5
H, m, H18, H18, H21, H24, H25), 1.76-1.62 (9 H, m, H2, H2,
H5, H11, H14, H21, H26, H29, H35), 1.60-1.53 (2 H, m, H8,
H24), 1.41 (1 H, dddd, J = 10.0,
9.0, 9.0, 2.5 Hz, H25), 1.27 (3 H, s, Me), 1.26 (3 H, s, Me), 1.16
(3 H, d, J = 6.0
Hz, 26-Me), 1.11 (3 H, s, Me), 1.00 (3 H, s, Me). ¹³C NMR
(150 MHz, C6D6): δ = 139.95,
138.84, 88.61, 86.22, 82.89, 81.83, 81.22, 80.45, 78.97, 78.67,
78.04, 77.82, 77.56 (2 ×), 77.24, 76.86, 75.81, 74.93,
73.43 (3 ×), 73.15, 72.26, 71.62, 71.45, 70.96, 69.80,
69.74, 58.75, 46.50, 43.76, 40.46, 39.87, 39.49, 37.70, 36.21, 35.95,
34.53, 32.74, 32.07, 30.15, 29.78, 23.56, 22.11, 20.59, 14.84, 14.30 (signals
of aromatic region are overlapped with solvent). IR (film): ν = 3437,
2928, 2874, 1453, 1378, 1340, 1286, 1204, 1068, 1025, 738, 698 cm-¹.
HRMS (ESI-TOF): m/z calcd for C57H80O15Na:
1027.5395 [M + Na]+;
found: 1027.5398.