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Synthesis 2009(17): 2992-3002
DOI: 10.1055/s-0029-1216941
DOI: 10.1055/s-0029-1216941
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Bioactive Natural Products by Asymmetric syn- and anti-Aldol Reactions
Further Information
Received
23 June 2009
Publication Date:
14 August 2009 (online)
Publication History
Publication Date:
14 August 2009 (online)
Abstract
The use of several variants of the asymmetric aldol reaction as key steps in the syntheses of bioactive target molecules is described.
Key words
natural products - asymmetric synthesis - chiral auxiliary - syn-aldol - anti-aldol - indanolamine
- 1
Evans DA.Fitch DM. J. Org. Chem. 1997, 62: 454 - 2
Mukaiyama T.Banno K.Narasaka K. J. Am. Chem. Soc. 1974, 96: 7503 -
3a
Ghosh AK.Kim J. Org. Lett. 2003, 5: 1063 -
3b
Ghosh AK.Onishi M. J. Am. Chem. Soc. 1996, 118: 2527 - 4
Ghosh AK.Kass J.Anderson DD.Xu X.Marian C. Org. Lett. 2008, 21: 4811 - 5
Ghosh AK.Xu X.Kim J.-H.Xu C.-X. Org. Lett. 2008, 10: 1001 - 6
Ghosh AK.Li J.-F. Synthesis 2006, 3015 -
7a
Kartner N.Riordan JR.Ling V. Science 1983, 221: 1285 -
7b
Pastan I.Gottesman MM. Annu. Rev. Med. 1991, 42: 277 - 8
Stratmann K.Burgoyne DL.Moore RE.Patterson GML.Smith CD. J. Org. Chem. 1994, 59: 7219 - 9
Endicott JA.Ling V. Annu. Rev. Biochem. 1989, 58: 137 - 10
Ghosh AK.Liu W.Xu Y.Chen Z. Angew. Chem.,Int. Ed. Engl. 1996, 35: 74 - 11
Ghosh AK.Duong TT.McKee SP. J. Chem. Soc., Chem. Commun. 1992, 1673 - 12
Schwarz RE.Hirsch CF.Sesin DF.Flor JE.Chartrain M.Fromtling RE.Harris GH.Salvatore MJ.Liesch JM.Yudin K. J. Ind. Microbiol. 1990, 5: 113 - 13
Smith CD.Zhang X.Mooberry SL.Patterson GML.Moore RE. Cancer Res. 1994, 54: 3779 - 14
Ghosh AK.Bischoff A. Org. Lett. 2000, 2: 1573 - 15
Ghosh AK.Swanson L. J. Org. Chem. 2003, 68: 9823 -
16a
Hochuli E.Kupfer E.Maurer R.Meiser W.Mercadel Y.Schmidt K. J. Antibiot. 1987, 40: 1086 -
16b
Weibel EK.Hadvary P.Kupfer E.Lengsfeld H. J. Antibiot. 1987, 40: 1081 -
17a
Borgstrom B. Biochem. Biophys. Acta. 1988, 962: 308 -
17b
Hadvary P.Sidler W.Meiser W.Vetter W.Wolfer H. J. Biol. Chem 1991, 266: 2021 - 18
Ghosh AK.Fidanze S. Org. Lett. 2000, 2: 2405 - 19
Knochel P.Seebach D. Synthesis 1982, 1017 -
20a
Evans DA.Chapman KT. Tetrahedron Lett. 1986, 27: 5939 -
20b
Evans DA.Chapman KT.Carreira EM. J. Org. Chem. 1988, 53: 3560 - 21
Shimojima Y.Hayashi H.Ooka T.Shibukawa M. Agric. Biol. Chem. 1982, 46: 1823 -
22a
Shimojima Y.Hayashi H. J. Med. Chem. 1983, 26: 1370 -
22b
Shimojima Y.Shirai T.Baba T.Hayashi H. J. Med. Chem. 1985, 28: 3 - 23
Ghosh AK.Bischoff A.Cappiello J. Org. Lett. 2001, 3: 2677 -
24a
Dondoni A.Fantin G.Fogagnolo M.Medici A.Pedrini P. Synthesis 1988, 685 -
24b
Dondoni A.Fogagnolo M.Medici A.Pedrini P. Tetrahedron Lett. 1985, 26: 5477 -
24c
Dondoni A.Perrone D.Semola MT. J. Org. Chem. 1995, 60: 7927 -
25a
Bertelli L.Fiaschi R.Napolitano E. Gazz. Chim. Ital. 1993, 123: 669 -
25b
Kotsuki H.Miyazaki A.Ochi M. Chem. Lett. 1992, 1255 -
25c
Superchi S.Minutolo F.Pini D.Salvadori P. J. Org. Chem. 1996, 61: 3183 - 26
Kobayashi J. In Comprehensive Natural Products Chemistry Vol. 8:Barton DHR.Nakanishi K.Meth-Cohn O. Elsevier; New York: 1999. p.619 - 27
Tsuda M.Endo T.Kobayashi J. J. Org. Chem. 2001, 66: 134 - 28
Ghosh AK.Liu C. J. Am. Chem. Soc. 2003, 125: 2374 - 29
Petasis NA.Bzowej EI. J. Am. Chem. Soc. 1990, 112: 6394 - 30
Ley SV.Lygo B.Wonnacott A. Tetrahedron Lett. 1989, 26: 535 -
31a
Crews P.Manes LV.Boehler M. Tetrahedron Lett. 1986, 27: 2797 -
31b
Zabriskie TM.Klocke JA.Ireland CM.Marcus AH.Molinski TF.Faulkner DJ.Xu C.Clardy JC. J. Am. Chem. Soc. 1986, 108: 3123 - 32
Inman W.Crews P. J. Am. Chem. Soc. 1986, 111: 2822 - 33
Bubb MR.Senderowicz AMJ.Sausville EA.Duncan KLK.Korn ED. J. Biol. Chem. 1994, 269: 14869 -
34a
Chu KS.Negrete GR.Konopelski JP. J. Org. Chem. 1991, 56: 5196 -
34b
Grieco PA.Hon YS. J. Am. Chem. Soc. 1988, 110: 1630 -
34c
Hanada Y.Shioiri T. Tetrahedron Lett. 2004, 35: 591 -
34d
Hirai Y.Yokota K.Momose T. Heterocycles 1994, 39: 603 -
34e
Imaeda T.Rao AV.Gurjar MK.Nallaganchu BR.Bhandari A. Tetrahedron Lett. 1993, 34: 7085 - 35
Ghosh AK.Moon DK. Org. Lett. 2007, 9: 2425 - 36
Ziegler FE. Acc. Chem. Res. 1977, 10: 227 - 37
Davis FA.Reddy RE.Szewczyk JM. J. Org. Chem. 1995, 60: 7037 - 38
West LM.Northcote PT.Battershill CN. J. Org. Chem. 2000, 65: 445 -
39a
Pryor DE.O’Brate A.Bilcer G.Diaz JF.Wang Y.Kabaki M.Jung MK.Andreu JM.Ghosh AK.Giannakakou P.Hamel E. Biochemistry 2002, 41: 9109 -
39b
Gaitanos TN.Buey RM.Diaz JF.Northcote PT.Teesdale-Spittle P.Andreu JM.Miller JH. Cancer Res. 2004, 64: 5063 - 40
Hood KA.West LM.Rouwe B.Northcote PT.Berridge MV.Wakefield SJ.Miller JH. Cancer Res. 2002, 62: 3356 -
41a
Jin M.Taylor RE. Org. Lett. 2005, 7: 1303 -
41b
Liao X.Wu Y.De Brabander JK. Angew. Chem. Int. Ed. 2003, 42: 1648 -
42a
Chen Z.-L.Zhou WS. Tetrahedron Lett. 2006, 47: 5289 -
42b
Engers DW.Bassindale MJ.Pagenkopf BL. Org. Lett. 2004, 6: 663 -
42c
Ghosh AK.Kim J.-H. Tetrahedron Lett. 2003, 44: 3967 -
42d
Gurjar MK.Pedduri Y.Ramana CV.Puranik VG.Gonnade RG. Tetrahedron Lett. 2004, 45: 387 -
42e
Liu B.Zhou WS. Org. Lett. 2004, 6: 71 -
42f
Owen RM.Roush WR. Org. Lett. 2005, 7: 3941 -
42g
Paterson I.Di Francesco ME.Kuhn T. Org. Lett. 2003, 5: 599 -
42h
Roulland E.Ermolenko MS. Org. Lett. 2005, 7: 2225 -
42i
Taylor RE.Jin M. Org. Lett. 2003, 5: 4959 - 43
Ghosh AK.Kim J.-H. Tetrahedron Lett. 2003, 44: 7659 - 44
Jadhav PK.Bhat KS.Perumal PT.Brown HC. J. Org. Chem. 1986, 51: 432 - 45
Ando KJ. J. Org. Chem. 1998, 63: 8411 - 46
Kolb HC.Van Nieuwenhze MS.Sharpless KB. Chem. Rev. 1994, 94: 2483 - 47
Seo C.Kim JH.Lee HK.Park SM.Sohn J.-H.Oh H. Tetrahedron Lett. 2008, 49: 29 - 48
Ghosh AK.Xu C.-X. Org. Lett. 2009, 11: 1963 -
49a
Mutou T.Suenaga K.Fujita T.Itoh T.Takada N.Hayamizu K.Kigoshi H.Yamada K. Synlett 1997, 199 -
49b
Paterson I.Smith JD. J. Org. Chem. 1992, 57: 3261 -
49c
Paterson I.Smith JD. Tetrahedron 1995, 51: 9413 - 50
Sepkowiz KA. N. Engl. J. Med. 2001, 344: 1764 -
51a
Grabar S.Pradier C.Le Corfec E.Lancar R.Allavena C.Bentata M.Berlureau P.Dupont C.Fabbro-Peray P.Poizot-Martin I.Costagliola D. AIDS 2000, 14: 141 -
51b
Pillay D.Bhaskaran K.Jurriaans S.Prins M.Masquelier B.Dabis F.Gifford R.Nielsen C.Pedersen C.Balotta C.Rezza G.Ortiz M.de Mendoza C.Kucherer C.Poggensee G.Gill J.Porter K. AIDS 2006, 20: 21 -
51c
Wainberg MA.Friedland G. J. Am. Med. Assoc. 1998, 279: 1977 -
52a
Ghosh AK.Shin DW.Swanson L.Krishnan K.Cho H.Hussain KA.Walters DE.Holland L.Buthod J. Farmaco 2001, 56: 29 -
52b
Ghosh AK.Kincaid JF.Cho W.Walters DE.Krishnan K.Hussain KA.Koo Y.Cho H.Rudall C.Holland L.Buthod J. Bioorg. Med. Chem. Lett. 1998, 8: 687 -
52c
Koh Y.Nakata H.Maeda K.Ogata H.Bilcer G.Devasamudram T.Kincaid JF.Boross P.Wang Y.-F.Tie Y.Volarath P.Gaddis L.Harrison RW.Weber IT.Ghosh AK.Mitsuya H. Antimicrob. Agents Chemother. 2003, 47: 3123 -
52d
Yoshimura K.Kato R.Kavlick MF.Nguyen A.Maroun V.Maeda K.Hussain KA.Ghosh AK.Gulnik SV.Erickson JW.Mitsuya H. J. Virol. 2002, 26: 1349 - 54
Miller JF.Andrews CW.Brieger M.Furfine ES.Hale MR.Hanlon MH.Hazen RJ.Kaldor I.McLean EW.Reynolds D.Sammond DM.Spaltenstein A.Tung R.Turner EM.Xu RX.Sherrill RG. Bioorg. Med. Chem. Lett. 2006, 16: 1788 -
55a
Ghosh AK.Kincaid JF.Walters DE.Chen Y.Chaudhuri NC.Thompson WJ.Culberson C.Fitzgerald PMD.Lee HY.McKee SP.Munson PM.Duong TT.Darke PL.Zugay JA.Schleif WA.Axel MG.Lin J.Huff JR. J. Med. Chem. 1996, 39: 3278 -
55b
Ghosh AK.Chen Y. Tetrahedron Lett. 1995, 36: 505 -
55c
Ghosh AK.Leshchenko S.Noetzel MJ. J. Org. Chem. 2004, 69: 7822 - 56
Quaedflieg PJLM.Kesteleyn BRR.Wigerinck PBTP.Goyvaerts NMF.Vijn RJ.Liebregts CSM.Kooistra JHMH.Cusan C. Org. Lett. 2005, 7: 5917
References
Darunavir received FDA approval on June 23, 2006: see http://www.fda.gov/bbs/topics/NEWS/2006NEW01395.html