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Synthesis 2007(23): 3741-3750
DOI: 10.1055/s-2007-990860
DOI: 10.1055/s-2007-990860
FEATUREARTICLE
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Furanomycin Derivatives by Gold-Catalyzed Cycloisomerization of α-Hydroxyallenes
Further Information
Received
17 September 2007
Publication Date:
29 October 2007 (online)
Publication History
Publication Date:
29 October 2007 (online)
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Abstract
The novel furanomycin analogues 8 and 17 were synthesized as mixture of two diastereomers using the gold-catalyzed cycloisomerization of α-hydroxyallenes as the key step. Compared to the traditional use of stoichiometric amounts of silver salts, gold catalysis is much more efficient for the cyclization of highly functionalized substrates.
Key words
allenes - amino acids - cycloisomerization - furanomycin - gold catalysis
- 1
Katagiri K.Tori K.Kimura Y.Yoshida T.Nagasaki T.Minato H. J. Med. Chem. 1967, 10: 1149 - 2
Von Nussbaum F.Brands M.Hinzen B.Weigand S.Häbich D. Angew. Chem. Int. Ed. 2006, 45: 5072 ; Angew. Chem. 2006, 118, 5194 -
3a
Semple JE.Wang PC.Lysenko Z.Joullié MM. J. Am. Chem. Soc. 1980, 102: 7505 -
3b
Kang SH.Lee SB. Chem. Commun. 1998, 761 -
3c
Zhang JH.Clive DLJ. J. Org. Chem. 1999, 64: 1754 -
3d
VanBrunt MP.Standaert RF. Org. Lett. 2000, 2: 705 -
3e
Zimmermann PJ.Blanarikova J.Jäger V. Angew. Chem. Int. Ed. 2000, 39: 910 ; Angew. Chem. 2000, 112, 936 -
4a
Kazmaier U.Pähler S.Endermann R.Häbich D.Kroll H.-P.Riedl B. Bioorg. Med. Chem. 2002, 10: 3905 -
4b
Jirgenson A.Marinozzi M.Pellicciari R. Tetrahedron 2005, 61: 373 -
4c
Lee JY.Schiffer G.Jäger V. Org. Lett. 2005, 7: 2317 -
4d
Chattopadhyay SK.Sarkar K.Karmakar S. Synlett 2005, 2083 - 5
Modern Allene Chemistry
Krause N.Hashmi ASK. Wiley-VCH; Weinheim: 2004. -
6a
Hoffmann-Röder A.Krause N. Org. Lett. 2001, 3: 2537 -
6b
Krause N.Hoffmann-Röder A.Canisius J. Synthesis 2002, 1759 -
6c
Hoffmann-Röder A.Krause N. Org. Biomol. Chem. 2005, 3: 387 -
6d
Deutsch C.Gockel B.Hoffmann-Röder A.Krause N. Synlett 2007, 1790 - 7
Gockel B.Krause N. Org. Lett. 2006, 8: 4485 -
8a
Morita N.Krause N. Org. Lett. 2004, 6: 4121 -
8b
Morita N.Krause N. Eur. J. Org. Chem. 2006, 4634 - 9
Morita N.Krause N. Angew. Chem. Int. Ed. 2006, 45: 1897 ; Angew. Chem. 2006, 118, 1930 - 10
Volz F.Krause N. Org. Biomol. Chem. 2007, 5: 1519 - 11
Krause N.Hoffmann-Röder A. Tetrahedron 2004, 60: 11671 -
12a
Garner P.Park JM. J. Org. Chem. 1987, 52: 2361 -
12b
McKillop A.Taylor RJK.Watson RJ.Lewis N. Synthesis 1994, 31 - 13
Pitsch W.Russel A.Zabel M.König B. Tetrahedron 2001, 57: 2345 - 14
Takahashi S.Kuroyama Y.Sonogashira K.Hagihara N. Synthesis 1980, 627 - 15
Adam W.Bialas J.Hadjiarapoglou L. Chem. Ber. 1991, 124: 2377 -
16a
Dess DB.Martin JC. J. Org. Chem. 1983, 48: 4155 -
16b
Boeckmann RK.Shao P.Mullins JJ. Org. Synth. Coll. Vol. X John Wiley & Sons; London: 2004. p.696 - 17
Bal BS.Childers WE.Pinnick HW. Tetrahedron 1981, 37: 2091 - 18
Corey EJ.Fuchs PL. Tetrahedron Lett. 1972, 13: 3769 -
19a
Reginato G.Mordini A.Degl’Innocenti A.Caracciolo M. Tetrahedron Lett. 1995, 36: 8275 -
19b
Reginato G.Mordini A.Caracciolo M. J. Org. Chem. 1997, 62: 6187 -
19c
Crisp GT.Jiang Y.-L.Pullman PJ.De Savi C. Tetrahedron 1997, 53: 17489 -
20a
Stille JK. Angew. Chem. Int. Ed. 1986, 25: 508 ; Angew. Chem. 1986, 98, 504 -
20b
Olivo HF.Velázquez F.Trevisan HC. Org. Lett. 2000, 2: 4055 -
20c
Evans DA.Burch JD. Org. Lett. 2001, 3: 503 -
20d
Trost BM.Gunzner JL.Dirat O.Rhee YH. J. Am. Chem. Soc. 2002, 124: 10396 -
20e
Centonze-Audureau S.Porée F.-H.Betzer J.-F.Brion J.-D.Pancrazi A.Ardisson J. Synlett 2005, 981 - 21
Shen W.Wang L. J. Org. Chem. 1999, 64: 8873 - 22 The ‘copper effect’ in Stille cross-coupling reactions is well documented:
Wang Y.Burton DJ. Org. Lett. 2006, 8: 1109 ; and references cited therein -
23a
Jiang B.Ma P. Synth. Commun. 1995, 25: 3641 -
23b
Cameron S.Khambay BPS. Tetrahedron Lett. 1998, 39: 1987 -
24a
Ohira S. Synth. Commun. 1989, 19: 561 -
24b
Müller S.Liepold B.Roth GJ.Bestmann HJ. Synlett 1996, 521 -
24c
Roth GJ.Liepold B.Müller DG.Bestmann HJ. Synthesis 2004, 59 -
24d For an improved synthesis of the Bestmann-Ohira reagent, see:
Pietruszka J.Witt A. Synthesis 2006, 4266 -
25a
Sonogashira K.Tohda Y.Hagihara N. Tetrahedron Lett. 1975, 16: 4467 -
25b
Doucet H.Hierso J.-C. Angew. Chem. Int. Ed. 2007, 46: 834 ; Angew. Chem. 2007, 119, 850, and references cited therein -
25c
Chinchilla R.Nájera C. Chem. Rev. 2007, 107: 874 ; and references cited therein - 26
Thorand S.Krause N. J. Org. Chem. 1998, 63: 8551 - 27
Fürstner A.Mendez M. Angew. Chem. Int. Ed. 2003, 42: 5355 ; Angew. Chem. 2003, 115, 5513 - 28
Elsevier CJ.Vermeer P. J. Org. Chem. 1989, 54: 3726 - 29
Bold G.Allmendinger T.Herold P.Moesch L.Schär H.-P.Duthaler RO. Helv. Chim. Acta 1992, 75: 865 -
30a
Thottumkara AP.Bowsher MS.Vinod TK. Org. Lett. 2005, 7: 2933 -
30b
More JD.Finney NS. Org. Lett. 2002, 4: 3001 -
30c
Schulze A.Giannis A. Synthesis 2006, 257 -
30d
Travis BR.Sivakumar M.Hollist GO.Borhan B. Org. Lett. 2003, 5: 1031 -
31a
Muller M.Mann A.Taddei M. Tetrahedron Lett. 1993, 34: 3289 -
31b
D’Aniello F.Falorni M.Mann A.Taddei M. Tetrahedron: Asymmetry 1996, 7: 1217 - 32
Elix JA.Kennedy JM. Aust. J. Chem. 1985, 38: 1857 - 33
Love BE.Jones EG. J. Org. Chem. 1999, 64: 3755 - 34
Huang WF.Xiao WJ. Chin. Chem. Lett. 1991, 2: 209 - 35
Johnson RL. J. Med. Chem. 1984, 27: 1351 -
36a
Buehl H.Gugel H.Kolshorn H.Meier H. Synthesis 1978, 536 -
36b
Dehmlow EV.Lissel M. Liebigs Ann. Chem. 1980, 1 -
36c
Tietze L.-F.Eicher T. Reaktionen und Synthesen im organisch-chemischen Praktikum und Forschungslaboratorium 2nd ed.: Thieme; Stuttgart: 1991. p.39