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DOI: 10.1055/s-2006-926376
The Iterative Synthesis of Acyclic Deoxypropionate Units and Their Implication in Polyketide-Derived Natural Products
Publikationsverlauf
Publikationsdatum:
08. März 2006 (online)
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Abstract
Interest in natural products containing deoxypropionate units has recently grown since the emergence of powerful synthetic strategies to access syn and anti stereoarrays. The purpose of this review is to focus on iterative methodologies leading to enantiopure carbon chains harboring two or more contiguous deoxypropionate units.
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1 Introduction
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2 Chiral Auxiliary Mediated Methods
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2.1 1,4-Conjugate Additions
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2.2 Enolate and Azaenolate Alkylations
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3 Asymmetric Allylic Substitution
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4 Nonchiral Auxiliary Mediated Methods
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4.1 Substrate and Conformational Control
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4.2 Substrate and Reagent Directed Control
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5 Indirect Methods
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6 Catalytic Methods
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6.1 Zr-Catalyzed Carboalumination Method
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6.2 Catalytic Organocuprate Addition Method
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7 Synopsis
Key words
natural products - enolates - conjugate additions - conformational analysis
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1a
Khosla C. Chem. Rev. 1997, 97: 2577 -
1b
Katz L. Chem. Rev. 1997, 97: 2557 -
2a
Nicolaou KC.Snyder SA. Classics in Total Synthesis II Wiley-VCH; Weinheim: 2003. -
2b
Nicolaou KC.Sorensen EJ. Classics in Total Synthesis Wiley-VCH; Weinheim: 1996. -
2c
Corey EJ.Cheng X.-M. The Logic of Chemical Synthesis Wiley & Sons; New York: 1989. - 3
Nicolaou KC.Vourloumis D.Winssinger N.Baran P. Angew. Chem. Int. Ed. 2000, 39: 44 - 4
Faul MM.Huff BE. Chem. Rev. 2000, 100: 2407 - Isolation:
-
5a
Sensi P.Greco AM.Ballotta R. Antibiot. Ann. 1960, 262 - Total synthesis:
-
5b
Nagaoka H.Rutsch W.Schmid G.Iio H.Johnson MR.Kishi Y. J. Am. Chem. Soc. 1980, 102: 7962 -
5c
Iio H.Nagaoka H.Kishi Y. J. Am. Chem. Soc. 1980, 102: 7965 - Isolation:
-
6a
Radics L. J. Chem. Soc., Chem. Commun. 1984, 599 -
6b
Grafe U.Schade W.Roth M.Radics L.Incze M.Ujszasky K. J. Antibiot. 1984, 37: 836 - Structure:
-
6c
Brooks HA.Poyser JP.Gardner D.King T. J. Antibiot. 1984, 37: 1501 - Total synthesis:
-
6d
Danishefsky SJ.Selnick HG.Zelle RE.DeNinno MP. J. Am. Chem. Soc. 1988, 110: 4368 -
6e
Defosseux M.Blanchard N.Meyer C.Cossy J. J. Org. Chem. 2004, 69: 4626 -
7a
Hoffmann RW. Angew. Chem. Int. Ed. 2000, 39: 2054 -
7b
Hoffmann RW. Angew. Chem., Int. Ed. Engl. 1987, 26: 489 - 8
Norte M.Fernandez JJ.Padilla A. Tetrahedron Lett. 1994, 35: 3413 - Isolation:
-
9a
Dawson JM.Farthing JE.Mashall PS.Middleton RF.O’Neill MJ.Shuttleworth A.Stylli C.Tait RM.Taylor PM.Widlman HG.Buss AD.Langley D.Hayes MV. J. Antibiot. 1992, 45: 639 - Total synthesis:
-
9b
Nicolaou KC.Nadin A.Leresche JE.Yue EW.La Greca S. Angew. Chem. Int. Ed. 1994, 33: 2190 -
9c
Caron S.Stoermer D.Mapp AK.Heathcock CH. J. Org. Chem. 1996, 61: 9115 -
9d
Tomooka K.Kikuchi M.Igawa K.Suzuki M.Keong P.-H.Nakai T. Angew. Chem. Int. Ed. 2000, 39: 4502 - Isolation:
-
10a
Rhodes A.Fantes KH.Boothroyd B.McGonagle MP.Crosse R. Nature 1961, 192: 952 - Structure:
-
10b
Brufani M.Cellai L.Keller-Schierlein W. Helv. Chim. Acta 1972, 55: 2329 - Total synthesis of venturicidin A and B aglycon:
-
10c
Akita H.Yamada H.Matsukura H.Nakata T.Oishi T. Tetrahedron Lett. 1990, 31: 1731 -
10d
Akita H.Yamada H.Matsukura H.Nakata T.Oishi T. Tetrahedron Lett. 1990, 31: 1735 - 11
Kohno J.Nishio M.Sakurai M.Kawano K.Hajime H.Kameda N.Kishi N.Yamashita T.Okuda T.Komatsubara S. Tetrahedron 1999, 55: 7771 -
12a
Isolation: see ref. 12b. Total synthesis: see ref. 33 and 57a.
-
12b
Norte M.Cataldo F.Gonzalez AG.Rodriguez ML.Ruiz-Perez C. Tetrahedron 1990, 46: 1669 - Stereochemistry and synthesis:
-
13a
Mori K.Kuwahara S. Tetrahedron 1986, 42: 5545 - Synthesis:
-
13b
Mori K.Kuwahara S. Tetrahedron 1986, 42: 5539 -
13c
Kaino M.Naruse Y.Ishihara K.Yamamoto H. J. Org. Chem. 1990, 55: 5814 -
13d
Morr M.Proppe C.Wray V. Liebigs Ann. 1995, 2001 - 14 Isolation:
Morr M.Wray V.Fortkamp J.Schmid RD. Liebigs. Ann. Chem. 1992, 433 - Isolation and structure:
-
15a
Chow S.Fletcher MT.Lambert LK.Gallagher OP.Moore CJ.Cribb BW.Allsopp PG.Kitching W. J. Org. Chem. 2005, 70: 1808 -
15b
Fletcher MT.Chow S.Lambert LK.Gallagher OP.Cribb BW.Allsopp PG.Moore CJ.Kitching W. Org. Lett. 2003, 5: 5083 - Structure:
-
16a
Ishiwata H.Nemoto M.Ojika M.Yamada K. J. Org. Chem. 1994, 59: 4710 - Total synthesis:
-
16b
Ishiwata H.Sone H.Kigoshi H.Yamada K. Tetrahedron 1994, 50: 12853 -
16c
Ghosh AK.Liu C. Org. Lett. 2001, 3: 635 -
16d
See also ref. 48
- Isolation:
-
17a
Berger J.Jampolsky LM.Goldberg MW. Arch. Biochem. 1949, 22: 476 -
17b
Lumb M.Macey PE.Spyvee J.Whitmarsh JM.Wright RD. Nature 1965, 206: 263 - Structure:
-
17c
Anderson BF.Herlt AJ.Rickards RW.Robertson GB. Aust. J. Chem. 1989, 42: 717 - Total synthesis: see ref. 23, 37a, 37b, and:
-
17d
Nagamitsu T.Takano D.Fukuda T.Otoguro K.Kuwajima I.Harigaya Y.Omura S. Org. Lett. 2004, 6: 1865 - Isolation:
-
18a
Nishiyama Y.Sugawara K.Tomita K.Yamamoto H.Kamei H.Oki T. J. Antibiot. 1993, 46: 921 - Structure:
-
18b
Suguwara K.Toda S.Moriyama T.Konishi M.Oki T. J. Antiobiot. 1993, 46: 928 -
19a
Wakabayashi T.Kageyama R.Naruse N.Tsukahara N.Funahashi Y.Kitoh K.Watanabe Y. J. Antibiot. 1997, 50: 671 -
19b
Eastwood EL.Schauss SE. Bioorg. Med. Chem. Lett. 2003, 13: 2235 - Isolation:
-
20a
Liu C.-M.Hermann TE. J. Biol. Chem. 1978, 253: 5892 - Synthesis:
-
20b
Hanessian S.Cooke NG.DeHoff B.Sakito Y. J. Am. Chem. Soc. 1990, 112: 5276 -
20c
Evans DA.Dow RL.Shih TL.Takacs JM.Zahler R. J. Am. Chem. Soc. 1990, 112: 5290 -
20d
Lautens M.Colucci JT.Hiebert S.Smith ND.Bouchain G. Org. Lett. 2002, 4: 1879 -
21a
Hoffmann RW.Gottlich R.Schopfer U. Eur. J. Org. Chem. 2001, 1865 -
21b
Hoffmann RW.Stahl M.Schopfer U.Frenking G. Chem. Eur. J. 1998, 4: 559 -
22a
Natta G.Corradini P. J. Polym. Sci. 1959, 39: 29 -
22b
Pucci S.Aglietto M.Luisi PL. J. Am. Chem. Soc. 1967, 89: 2787 -
22c
Golam O.Goren Z.Biali SE. J. Am. Chem. Soc. 1990, 112: 9300 -
22d
Nolte RJM. Chem. Soc. Rev. 1994, 23: 11 -
22e
Okamoto Y.Nakano T. Chem. Rev. 1994, 94: 349 -
22f
Green MM.Park J.-W.Sato T.Teramoto A.Lifson S.Selinger R.Selinger JV. Angew. Chem. Int. Ed. 1999, 38: 3138 - 23
Hanessian S.Yang Y.Giroux S.Mascitti V.Ma J.Raeppel F. J. Am. Chem. Soc. 2003, 125: 13784 -
24a
Calter MA.Liao W.Strauss JA. J. Org. Chem. 2001, 66: 7500 -
24b
Calter MA.Liao W. J. Am. Chem. Soc. 2002, 124: 13127 -
25a
Evans DA.Morrissey MM. J. Am. Chem. Soc. 1984, 106: 3866 -
25b
Evans DA.Morrissey MM.Dow RL. Tetrahedron Lett. 1985, 26: 6005 -
25c
Marshall JA.Blough BF. J. Org. Chem. 1990, 55: 1540 -
25d
Brown JM. Angew. Chem. Int. Ed. 1987, 26: 190 - Ring-opening strategies:
-
26a
Ref. 13c.
-
26b
Hanaki N.Ishihara K.Kaino M.Naruse Y.Yamamoto H. Tetrahedron 1996, 52: 7297 -
26c
Gambacorta A.Tofani D.Lupattelli P.Tafi A. Tetrahedron Lett. 2002, 43: 2195 -
26d
Ref. 20d.
-
26e
Sugimura T.Sato Y.Im CY.Okuyama T. Org. Lett. 2004, 6: 4439 - Catalytic desymmetrization:
-
26f
Yamamoto K.Nishioka T.Oda T. J. Chem. Soc. Chem. Commun. 1985, 1717 -
26g
Hiratake J.Inagaki M.Yamamoto Y.Oda T. J. Chem. Soc., Perkin Trans. 1 1987, 1053 - Optical or enzymatic resolution:
-
26h
Fujita K.Mori K. Eur. J. Org. Chem. 2001, 493 -
26i
Ref. 13a.
-
26j
Datel DV.VanMiddlesworth F.Donaubauer J.Garnett P.Sih CJ. J. Am. Chem. Soc. 1986, 108: 4603 -
26k
Sefkow M.Neidlein A.Sommerfeld T.Sternfeld F.Maestro NA.Seebach D. Liebigs Ann. Chem. 1994, 719 - Cope rearrangement:
-
26l
Tomooka K.Nagasawa A.Wei S.-Y.Nakai T. Tetrahedron Lett. 1996, 37: 8895 - Miscellaneous:
-
26m
Mori I.Bartlett PA.Heathcock CH. J. Org. Chem. 1990, 55: 5966 -
26n
Wilson SR.Price MF. J. Am. Chem. Soc. 1982, 104: 1124 - 27
Oppolzer W.Maretti R.Bernardelli G. Tetrahedron Lett. 1986, 27: 4713 - 28 For a review, see:
Oppolzer W. Tetrahedron 1987, 43: 1969 - 29
Capon RJ.Faulkner DJ. J. Org. Chem. 1984, 49: 2506 - 30
Ogawa T.Suemune H.Sakai K. Chem. Pharm. Bull. 1993, 41: 1652 - 31
Decicco CP.Grover P. J. Org. Chem. 1996, 61: 3534 - 32
Abiko A.Moriya O.Filla SA.Masamune S. Angew. Chem. Int. Ed. 1995, 34: 793 - 33
Abiko A.Masamune S. Tetrahedron Lett. 1996, 37: 1081 - 35
Hanessian S.Thavonekham B.DeHoff B. J. Org. Chem. 1989, 54: 5831 - 36
Myers AG.Yang BH.Chen H.Kopecky D. Synlett 1997, 457 -
37a
Duffey MO.LeTiran A.Morken JP. J. Am. Chem. Soc. 2003, 127: 1458 -
37b
Vong BG.Kim SH.Abraham S.Thedorakis EA. Angew. Chem. Int. Ed. 2004, 43: 3947 - 38
Job A.Janeck CF.Bettray W.Peters R.Enders D. Tetrahedron 2002, 58: 2253 - 39
Birkbeck AA.Enders D. Tetrahedron Lett. 1998, 39: 7823 -
40a
Williams DR.Kissel WS.Li JJ.Mullins RJ. Tetrahedron Lett. 2002, 43: 3723 -
40b
Williams DR.Nold AL.Mullins RJ. J. Org. Chem. 2004, 69: 5374 - 41
Nicolás E.Russel KC.Hruby VJ. J. Org. Chem. 1993, 58: 766 - 42
Spino C.Beaulieu C.Lafreniere J. J. Org.Chem. 2000, 65: 7091 - 43
Spino C.Allan M. Can. J. Chem. 2004, 82: 177 - 44
Breit B.Herber C. Angew. Chem. Int. Ed. 2004, 43: 3790 - 45
Breit B. Angew. Chem. Int. Ed. 1998, 37: 525 - 46
Bornscheuer UT.Kazlauskas RJ. In Hydrolases in Organic Synthesis Wiley-VCH; Weinheim: 1999. p.70-72 - 47
Breit B.Herber C. Angew. Chem. Int. Ed. 2005, 44: 5267 - 48
Hanessian S.Mascitti V.Giroux S. Proc. Natl. Acad. Sci. U.S.A. 2004, 101: 11996 -
49a
Hanessian S.Sumi K. Synthesis 1991, 1083 -
49b
Hanessian S.Gai Y.Wang W. Tetrahedron Lett. 1996, 37: 7473 -
49c
Hanessian S.Ma J.Wang W.Gai Y. J. Am. Chem. Soc. 2001, 123: 10200 -
50a
Hanessian S.Wang W.Gai Y. Tetrahedron Lett. 1996, 37: 7477 -
50b
Hanessian S.Raghavan S. Bioorg. Med. Chem. Lett. 1994, 4: 1697 - 51
Hanessian S.Wang W.Gai Y.Olivier E. J. Am. Chem. Soc. 1997, 119: 10034 - 52
Katsuki T.Sharpless KB. J. Am. Chem. Soc. 1980, 102: 5974 - 53
Breit B.Demel P. Tetrahedron 2000, 56: 2833 - 54
Charette AB.Juteau H. J. Am. Chem. Soc. 1994, 116: 2651 - 55
Charette AB.Naud J. Tetrahedron Lett. 1998, 39: 7259 - 56
Barton DHR.McCombie SW. J. Chem. Soc., Perkin Trans. 1 1975, 1574 -
57a
Magnin-Lachaux M.Tan Z.Liang B.Negishi E.-I. Org. Lett. 2004, 6: 1425 -
57b
Negishi E.-I.Tan Z.Liang B.Novak T. Proc. Natl. Acad. Sci. U.S.A. 2004, 101: 5782 - See also:
-
57c
Kondakov D.Negishi E.-I. J. Am. Chem. Soc. 1996, 118: 1577 -
57d
Kondakov D.Negishi E.-I. J. Am. Chem. Soc. 1995, 117: 10771 - 58
Corey EJ.Enders D.Bock MG. Tetrahedron Lett. 1976, 1: 7 - 59
Tan Z.Negishi E.-I. Angew. Chem. Int. Ed. 2004, 43: 2911 - 60
Novak T.Tan Z.Liang B.Negishi E.-I. J. Am. Chem. Soc. 2005, 127: 2838 - 61
Lopez F.Harutyunyan SR.Meetsma A.Minnaard AJ.Feringa BL. Angew. Chem. Int. Ed. 2005, 44: 2752 - 62
Des Mazery R.Pullez M.Lopez F.Harutyunyan SR.Minnaard AJ.Feringa BL. J. Am. Chem. Soc. 2005, 127: 9966 - 63
Evans DA.Nelson JV.Vogel E.Taber TR. J. Am. Chem. Soc. 1981, 103: 3099 - 64
Fukuyama T.Tokuyama H. Aldrichimica Acta 2004, 37: 87 - 65
Carreno MC.Garcia Ruano JL.Martin AM.Pedegral C.Rodriguez JH.Rubio A.Sanchez J.Solladié G. J. Org. Chem. 1990, 55: 2120
References
Both enantiomers of 2-methyl-3-hydroxymethyl propionic acid are available commercially.