RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
Synlett 2010(6): 982-986
DOI: 10.1055/s-0029-1219540
DOI: 10.1055/s-0029-1219540
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
Exploratory Studies en Route to 5-Alkyl-Hyacinthacines: Synthesis of 5-epi-(-)-Hyacinthacine A3 and (-)-Hyacinthacine A3
Weitere Informationen
Received
22 December 2009
Publikationsdatum:
23. Februar 2010 (online)
Publikationsverlauf
Publikationsdatum:
23. Februar 2010 (online)
![](https://www.thieme-connect.de/media/synlett/201006/lookinside/thumbnails/10.1055-s-0029-1219540-1.jpg)
Abstract
Synthesis of 5-epi-(-)-hyacinthacine A3 and (-)-hyacinthacine A3 has been achieved from the d-xylose-derived polyhydroxylated cyclic nitrone. Our synthetic strategy is potentially general and flexible for the synthesis of both epimers of 5-alkyl-hyacinthacines.
Key words
nitrone - α-amino nitrile - iminosugars - polyhydroxylated pyrrolizidine - hyacinthacine
- Supporting Information for this article is available online:
- Supporting Information
-
1a
Compain P.Martin O. Iminosugars: From Synthesis to Therapeutic Applications J. Wiley and Sons; Chichester: 2007. -
1b
Stütz AE. Iminosugars as Glycosidase Inhibitors: Nojirimycin and Beyond Wiley-VCH; Weinheim: 1999. -
1c
Asano N.Nash RJ.Molyneux RJ.Fleet GWJ. Tetrahedron: Asymmetry 2000, 11: 1645 -
1d
Watson AA.Fleet GWJ.Asano N.Molyneux RJ.Nash RJ. Phytochemistry 2001, 56: 265 -
1e
Lillelund VH.Jensen HH.Liang X.Bols M. Chem. Rev. 2002, 102: 515 -
1f
Whalen LJ.Wong C.-H. Aldrichimica Acta 2006, 39: 63 -
2a
Wrodnigg TM.Steiner AJ.Ueberbacher BJ.
Anti-Cancer Agents Med. Chem. 2008, 8: 77 -
2b
Gerber-Lemaire S.Juillerat-Jeanneret L. Mini-Rev. Med. Chem. 2006, 6: 1043 -
3a
Greimel P.Spreitz J.Stütz AE.Wrodnigg TM. Curr. Top. Med. Chem. 2003, 3: 513 -
3b
Robina I.Moreno-Vargas AJ.Carmona AT.Vogel P. Curr. Drug Metab. 2004, 5: 329 -
4a
Butters TD.Dwek RA.Platt FM. Chem. Rev. 2000, 100: 4683 -
4b
Fan J.-Q. Trends Pharmacol. Sci. 2003, 24: 355 - 5
Ye XS.Sun F.Liu M.Li Q.Wang Y.Zhang G.Zhang LH.Zhang XL. J. Med. Chem. 2005, 48: 3688 -
6a
Kato A.Adachi I.Miyauchi M.Ikeda K.Komae T.Kizu H.Kameda Y.Watson AA.Nash RJ.Wormald MR.Fleet GWJ.Asano N. Carbohydr. Res. 1999, 316: 95 -
6b
Asano N.Kuroi H.Ikeda K.Kizu H.Kameda Y.Kato A.Adachi I.Watson AA.Nash RJ.Fleet GWJ. Tetrahedron: Asymmetry 2000, 11: 1 -
6c
Yamashita T.Yasuda K.Kizu H.Kameda Y.Watson AA.Nash RJ.Fleet GWJ.Asano N. J. Nat. Prod. 2002, 65: 1875 -
6d
Asano N.Ikeda K.Kasahara M.Arai Y.Kizu H. J. Nat. Prod. 2004, 67: 846 -
6e
Kato A.Kato N.Adachi I.Hollinshead J.Fleet GWJ.Kuriyama C.Ikeda K.Asano N.Nash RJ. J. Nat. Prod. 2007, 70: 993 -
7a
Rambaud L.Compain P.Martin OR. Tetrahedron: Asymmetry 2001, 12: 1807 -
7b
Izquierdo I.Plaza MT.Franco F. Tetrahedron: Asymmetry 2002, 13: 1581 -
7c
Cardona F.Faggi E.Liguori F.Cacciarini M.Goti A. Tetrahedron Lett. 2003, 44: 2315 -
7d
Chabaud L.Landais Y.Renaud P. Org. Lett. 2005, 7: 2587 -
7e
Desvergnes S.Py S.Vallee Y. J. Org. Chem. 2005, 70: 1459 -
7f
Dewi-Wülfing P.Blechert S. Eur. J. Org. Chem. 2006, 1852 -
7g
Calveras J.Casas J.Parella T.Joglar J.Clapes P. Adv. Synth. Catal. 2007, 349: 1661 -
7h
Zhou L.Chen J.Cao XP. Synthesis 2007, 1359 -
7i
Donohoe TJ.Thomas RE.Cheeseman MD.Rigby CL.Bhalay G.Linney ID. Org. Lett. 2008, 10: 3615 -
7j
Sengoku T.Satoh Y.Oshima M.Takahashi M.Yoda H. Tetrahedron 2008, 64: 8052 -
7k
Kaliappan KP.Das P. Synlett 2008, 841 -
7l
Chandrasekhar S.Parida BB.Rambabu C. J. Org. Chem. 2008, 73: 7826 -
7m
Affolter O.Baro A.Frey W.Laschat S. Tetrahedron 2009, 65: 6626 -
7n
Reddy PV.Koos P.Veyron A.Greene AE.Delair P. Synlett 2009, 1141 -
7o
Ribes C.Falomir E.Carda M.Marco JA. Tetrahedron 2009, 65: 6965 -
8a
Asano N.Ikeda K.Yu L.Kato A.Takebayashi K.Adachi I.Kato I.Ouchi H.Takahata H.Fleet G. Tetrahedron: Asymmetry 2005, 16: 223 -
8b
Yu C.-Y.Asano N.Ikeda K.Wang M.-X.Butters TD.Wormald MR.Dwek RA.Winters AL.Nash RJ.Fleet GWJ. Chem. Commun. 2004, 1936 -
8c
Yu CY.Huang MH. Org. Lett. 2006, 8: 3021 -
8d
Davis BB.Nash RJ.Watson AA.Griffiths RC.Jones MG.Smith C.Fleet GWJ. Tetrahedron Lett. 1996, 37: 8565 - For recent work on polyhydroxylated cyclic nitrones, see:
-
9a
Holzapfel CW.Crous R. Heterocycles 1998, 48: 1337 -
9b
Duff FJ.Vivien V.Wightman RH. Chem. Commun. 2000, 2127 -
9c
Tamura O.Toyao A.Ishibashi H. Synlett 2002, 1344 -
9d
Carmona AT.Wightman RH.Robina I.Vogel P. Helv. Chim. Acta 2003, 86: 3066 -
9e
Cicchi S.Marradi M.Vogel P.Goti A. J. Org. Chem. 2006, 71: 1614 -
9f
Desvergnes SP.Vallee Y.Py S. Org. Lett. 2008, 10: 2967 -
9g
Kaliappan KP.Das P.Chavan ST.Sabharwal SG. J. Org. Chem. 2009, 74: 6266 -
9h
Racine E.Bello C.Gerber-Lemaire S.Vogel P.Py S. J. Org. Chem. 2009, 74: 1766 -
9i
Tamayo JA.Franco F.Lo Re D.Sanchez-Cantalejo F. J. Org. Chem. 2009, 74: 5679 -
9j
Tsou E.-L.Yeh Y.-T.Liang P.-H.Cheng W.-C. Tetrahedron 2009, 65: 93 -
9k
Cardona F.Parmeggiani C.Faggi E.Bonaccini C.Gratteri P.Sim L.Gloster TM.Roberts S.Davies GJ.Rose DR.Goti A. Chem. Eur. J. 2009, 15: 1627 -
9l
Brandi A.Cardona F.Cicchi S.Cordero FM.Goti A. Chem. Eur. J. 2009, 15: 7808 - For recent reviews of cycloaddition of nitrones, see:
-
10a
Gothelf KV.Jørgensen KA. Chem. Rev. 1998, 98: 863 -
10b
Brandi A.Cicchi S.Cordero FM.Goti A. Chem. Rev. 2003, 103: 1213 -
11a
Chang Z.-Y.Coates RM. J. Org. Chem. 1990, 55: 3464 -
11b
Chang Z.-Y.Coates RM. J. Org. Chem. 1990, 55: 3475 - 12
Cardona F.Moreno G.Guarna F.Vogel P.Schuetz C.Merino P.Goti A. J. Org. Chem. 2005, 70: 6552 -
13a
Ballini R.Marcantoni E.Petrini M. J. Org. Chem. 1992, 57: 1316 -
13b
Giovannini R.Marcantoni E.Petrini M. J. Org. Chem. 1995, 60: 5706 -
14a
Merino P.Franco S.Merchan FL.Tejero T. Synlett 2000, 442 -
14b
Merino P. In Science of Synthesis Vol. 27:Padwa A. Thieme; Stuttgart: 2004. p.511-580 -
14c
Merino P. C. R. Chim. 2005, 8: 775 -
15a
Lombardo M.Trombini C. Synthesis 2000, 759 -
15b
Lombardo M.Fabbroni S.Trombini C. J. Org. Chem. 2001, 66: 1264 - 16
Wang W.-B.Huang M.-H.Li Y.-X.Rui P.-X.Hu X.-G.Zhang W.Su J.-K.Zhang Z.-L.Zhu J.-S.Xu W.-H.Xie X.-Q.Jia Y.-M.Yu C.-Y. Synlett 2010, 488 - 17
Lee TV.Porter JR. Org. Synth., Coll. Vol. IX 1998, 643 - 18
Merino P.Revuelta J.Tejero T.Cicchi S.Goti A. Eur. J. Org. Chem. 2004, 776 - 19
Merino P.Delso I.Tejero T.Cardona F.Marradi M.Faggi E.Parmeggiani C.Goti A. Eur. J. Org. Chem. 2008, 2929 ; and references cited therein - 20
Dhavale DD.Gentilucci L.Piazza MG.Trombini C. Liebigs Ann. Chem. 1992, 1289 -
21a
Enders D.Shilvock JP. Chem. Soc. Rev. 2000, 29: 359 -
21b
Husson H.-P.Royer J. Chem. Soc. Rev. 1999, 28: 383 - 22
Cook AG. Enamines: Synthesis, Structure, and Reactions Marcel Dekker; New York: 1988. p.275-346 - 23
Bruylants P. Bull. Soc. Chim. Belg. 1924, 33: 467 -
24a
Royer J.Husson H.-P. Tetrahedron Lett. 1986, 26: 1515 -
24b
Polniaszek RP.Belmont SE. J. Org. Chem. 1991, 56: 4868 -
26a
Guerrier L.Royer J.Grierson DS.Husson H.-P.
J. Am. Chem. Soc. 1983, 105: 7754 -
26b
Agami C.Couty F.Evano G. Org. Lett. 2000, 2: 2085 - 27
Yue C.Royer J.Husson H.-P. J. Org. Chem. 1992, 57: 4211 - 28
Sun P.Sun C.Weinreb SM. Org. Lett. 2001, 3: 3507
References and Notes
The crystal structure of 19 has been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition number: CCDC 756239.