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Liebigs Annalen der Chemie

Volumn 1986, Issue 7, 1986, Pages 1281-1308

(+)‐11,11′‐Di‐O‐methylelaiophylidene – preparation from elaiophylin and total synthesis from (R)‐3‐hydroxybutyrate and (S)‐malate

(6) Seebach, Dieter a Chow, Hak‐Fun a Jackson, Richard F W a Sutter, Marius A a Thaisrivongs, Suvit a Zimmermann, Jürg a

a ETH ZURICH (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

11,11' DI O METHYLELAIOPHYLIDENE; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; THEORETICAL STUDY;

EID: 0022995478 PISSN: 01702041 EISSN: 10990690 Source Type: Journal
DOI: 10.1002/jlac.198619860714 Document Type: Article

Times cited : (84)

References (116)

1
- 0002417989
- Struktur und Biogenese der Makrolide
- For the terms “macrolide”, “macrodiolide”, and “macrotetrolide” see for instance
- (1957) Angewandte Chemie , vol.69 , pp. 50
- Woodward, R.B.¹

2
- 84981838869
- (1962) Helvetica Chimica Acta , vol.45 , pp. 129
- Dominguez, J.¹ Dunitz, J.D.² Gerlach, H.³ Prelog, V.⁴

3
- 0015187424
- D. Mikloš
- (1971) Helv. Chim. Acta , vol.54 , pp. 1709
- Dunitz, J.D.¹ Hawley, D.M.² White, D.N.J.³ Berlin, Y.⁴ Marušić, R.⁵ Prelog, V.⁶

4
- 0021880919
- Most recent review article on macrolide synthesis
- (1985) Tetrahedron , vol.41 , pp. 3569
- Paterson, J.¹ Mansuri, M.M.²

5
- 0002549746
- J. Chem. Soc. C , vol.1966 , pp. 230
- Grove, J.F.¹ Speake, R.N.² Ward, G.³

6
- 0014448599
- J. Chem. Soc. C , vol.1969 , pp. 911
- Powell, J.W.¹ Whalley, W.B.²

7
- 84985245787
- 6b, and Grahamimycin A and B; see:, U. S. Patent 4,220,718
- (1980)
- Gurusiddaiah, S.¹ Ronald, R.C.² Magnuson, J.A.³ McFadden, B.A.⁴

8
- 84985245782
- 879h
- (1981) Chem. Abstr. , vol.94 , pp. 28

9
- 2642637150
- (6a)
- Tetrahedron Lett. , vol.1968 , pp. 5497
- McMillan, J.¹ Price, R.J.²

10
- 37049132600
- (6b)
- J. Chem. Soc., Perkin Trans. 1 , vol.1973 , pp. 1487
- MacMillan, J.¹ Simpson, T.J.²

11
- 0000972127
- Revidierte Struktur des Makrodiolids Colletodiol
- (1981) Helvetica Chimica Acta , vol.64 , pp. 1796
- Amstutz, R.¹ Hungerbühler, E.² Seebach, D.³

12
- 0000448358
- 2163
- (1984) Tetrahedron Lett. , vol.25 , pp. 2159
- Tsutsui, H.¹ Mitsunobu, O.²

13
- 0021326546
- (1984) Tetrahedron Lett. , vol.25 , pp. 2209
- Schnurrenberger, P.¹ Hungerbühler, E.² Seebach, D.³

14
- 0018872686
- (1980) Tetrahedron Lett. , vol.21 , pp. 681
- Ronald, R.C.¹ Gurusiddaiah, S.²

15
- 0020028387
- (1982) Tetrahedron Lett. , vol.23 , pp. 159
- Seebach, D.¹ Seidel, W.²

16
- 0020699934
- (1983) Tetrahedron Lett. , vol.24 , pp. 287
- Ghiringelli, D.¹

17
- 0021957662
- (1985) J. Org. Chem. , vol.50 , pp. 470
- Hillis, L.R.¹ Ronald, R.C.²

18
- 85007865127
- (1961) J. Agric. Chem. Soc. Jpn. , vol.35 , pp. 257
- Ishibashi, K.¹

19
- 84985261790
- (1962) J. Antibiot., Ser. A , vol.15 , pp. 166
- Ishibashi, K.¹

20
- 0007647359
- Tetrahedron Lett. , vol.1965 , pp. 4675
- Nozoe, S.¹ Hirai, K.² Tsuda, K.³ Ishibashi, K.⁴ Shirasaka, M.⁵ Grove, J.F.⁶

21
- 84980176320
- J. Chem. Soc. C , vol.1971 , pp. 2261
- Grove, J.F.¹

22
- 0007107520
- Synthese und Bestimmung der absoluten Konfiguration von Pyrenophorin und Vermiculin
- (1977) Angewandte Chemie , vol.89 , pp. 270
- Seebach, D.¹ Seuring, B.² Kalinowski, H.O.³ Lubosch, W.⁴ Renger, B.⁵

23
- 0017480093
- (1977) Angew. Chem., Int. Ed. Engl. , vol.16 , pp. 264

24
- 37049141870
- J. Chem. Soc., Chem. Commun. , vol.1972 , pp. 1031
- Colvin, E.W.¹ Purcell, T.A.² Raphael, R.A.³

25
- 0016909798
- J. Chem. Soc., Perkin Trans. 1 , vol.1976 , pp. 1718
- Colvin, E.W.¹ Purcell, T.A.² Raphael, R.A.³

26
- 0017763528
- (1977) Helv. Chim. Acta , vol.60 , pp. 2860
- Gerlach, H.¹ Oertle, K.² Thalmann, A.³

27
- 0018242403
- Liebigs Ann. Chem. , vol.1978 , pp. 2044
- Seuring, B.¹ Seebach, D.²

28
- 2642665970
- Tetrahedron Lett. , vol.1978 , pp. 2371
- Bakuzis, P.¹ Bakuzis, M.L.F.² Weingartner, T.F.³

29
- 0001247704
- (1979) J. Org. Chem. , vol.44 , pp. 3448
- Trost, B.M.¹ Gowland, F.W.²

30
- 0342726729
- The reaction of 2-(trialkylsiloxy)furans with lead(IV) acetate. The synthesis of dl-pyrenophorin.
- (1980) Bulletin of the Chemical Society of Japan , vol.53 , pp. 1061
- Asaoka, M.¹ Yanagida, N.² Sugimura, N.³ Takei, H.⁴

31
- 0000429775
- (1981) Tetrahedron Lett. , vol.22 , pp. 735
- Asaoka, M.¹ Mukuta, T.² Takei, H.³

32
- 0019848138
- (1981) J. Org. Chem. , vol.46 , pp. 3137
- Hase, T.A.¹ Ourila, A.² Holmberg, C.³

33
- 84981407082
- Liebigs Ann. Chem. , vol.1981 , pp. 2272
- Mali, R.S.¹ Pohmakotr, M.² Weidmann, B.³ Seebach, D.⁴

34
- 84985283074
- Chem. Lett. , vol.1982 , pp. 1795
- Fujisawa, T.¹ Takeuchi, M.² Sato, T.³

35
- 0011782538
- (1983) Tetrahedron Lett. , vol.24 , pp. 4283
- Labadie, J.W.¹ Stille, J.K.²

36
- 0000125818
- (1984) Tetrahedron Lett. , vol.25 , pp. 5763
- Derguini, F.¹ Linstrumelle, G.²

37
- 0021176263
- (1984) Tetrahedron Lett. , vol.25 , pp. 2883
- Dumont, W.¹ Vermeyen, C.² Krief, A.³

38
- 0039392836
- (1984) Tetrahedron Lett. , vol.25 , pp. 5759
- Breuilles, P.¹ Uguen, D.²

39
- 0021844749
- (1985) Tetrahedron Lett. , vol.26 , pp. 1989
- Wakamatsu, T.¹ Yamada, S.² Ozaki, Y.³ Ban, Y.⁴

40
- 0015329653
- VERMICULINE, A NEW ANTIPROTOZOAL ANTIBIOTIC FROM PENICILLIUM VERMICULATUM
- (1972) The Journal of Antibiotics , vol.25 , pp. 208
- Furka, J.¹ Memec, P.² Kuhr, I.³

41
- 0016384505
- (1974) J. Am. Chem. Soc. , vol.96 , pp. 5954
- Boeckman, R.K.¹ Fayos, J.² Clardy, J.³

42
- 84985243486
- Review covering the literature on vermiculine syntheses up to 1982: Synform 1983, 138.

43
- 1542413044
- (1983) Gazz. Chim. Ital. , vol.113 , pp. 461
- Traverso, G.¹ Pirillo, D.² Gazzaniga, A.³

44
- 0018620143
- (1979) J. Antibiot. , vol.32 , pp. 874
- Westley, W.J.¹ Liu, M.C.² Evans, H.R.³ Blount, J.F.⁴

45
- 0003513025
- (1984) Tetrahedron Lett. , vol.25 , pp. 5881
- Schregenberger, Ch.¹ Seebach, D.²

46
- 0001608835
- (1959) J. Microbiol. , vol.7 , pp. 207
- Arcamone, F.M.¹ Bertazzoli, C.² Ghione, M.³ Scotti, T.⁴

47
- 72849154141
- 51
- (1960) J. Antibiot., Ser. A , vol.13 , pp. 46
- Arai, M.¹

48
- 0007826131
- (1972) Farmatsya (Sofia) , vol.22 , pp. 3
- Khlebarova, E.I.¹ Georgieva‐Borisova² Sheikova, G.N.³ Blinov, N.O.⁴

49
- 84985210891
- Hoechst AG, (Erf.), Deutsche Offenlegungsschrift, DE 32 48 280 (5. Juli 84).
- Vértesy, L.¹ Paulus, E.²

50
- 0014149220
- Chemical Studies on Azalomycins. I. Preliminary Study on Azalomycin-B.
- 1657
- (1967) CHEMICAL & PHARMACEUTICAL BULLETIN , vol.15 , pp. 1651
- Tokahashi, S.¹ Arai, M.² Ohki, E.³

51
- 0014149969
- Chemical Studies on Azalomycins. III. Alkaline Degradation of Azalomycin-B.
- (1967) CHEMICAL & PHARMACEUTICAL BULLETIN , vol.15 , pp. 1726
- Tokahashi, S.¹ Ohki, E.²

52
- 84985100261
- (1981) Helvetica Chimica Acta , vol.64 , pp. 407
- Kaiser, H.¹ Keller‐Schierlein, W.²

53
- 0020052802
- (1982) Helv. Chim. Acta , vol.65 , pp. 262
- Neupert‐Laves, K.¹ Dobler, M.²

54
- 0043114409
- (1982) Tetrahedron Lett. , vol.23 , pp. 1207
- Ley, S.V.¹ Neuhaus, D.² Williams, D.J.³

55
- 84985281413
- Hoechst AG, Frankfurt/Main, personal communication
- (1983)
- Paulus, E.F.¹

56
- 0021186834
- Molecular modelling
- (1984) Tetrahedron Lett. , vol.25 , pp. 4325
- Corey, E.J.¹ Ponder, J.W.²

57
- 84985286849
- part of the projected Ph. D. thesis, ETH (Zürich)
- Brändli, U.¹

58
- 37049110062
- J. Chem. Soc., Chem. Commun. , vol.1980 , pp. 904
- Bates, G.S.¹ Ramaswamy, S.²

59
- 0000246435
- Oxidation von α,β-ungesättigten Estern und Lactonen mit Selendioxid zu γ-Oxo- oder γ-Hydroxy-Derivaten; Synthese von (±)-A 26771 B und Norpyrenophorin
- (1985) Angewandte Chemie , vol.97 , pp. 784
- Bestmann, H.J.¹ Schobert, R.²

60
- 84985609322
- (1985) Angew. Chem., Int. Ed. Engl. , vol.24 , pp. 791

61
- 0020625140
- Liebigs Ann. Chem. , vol.1983 , pp. 939
- Sutter, M.A.¹ Seebach, D.²

62
- 0007631037
- (1976) Nachr. Chem. Tech. Lab. , vol.24 , pp. 415
- Seebach, D.¹ Kalinowski, H.O.²

63
- 0003433653
- Pergamon Press, Oxford
- (1983) Total Synthesis of Natural Products: The Chiron Approach
- Hanessian, S.¹

64
- 0002874969
- Edit, J. D. Morrison, J. W. Scott, Academic Press, Inc, New York
- (1984) Asymmetric Synthesis , vol.4 , pp. 1
- Scott, J.W.¹

65
- 0003598098
- 115ff., (Edit. R. Scheffold), Salle + Sauerländer, Frankfurt/Main and Aarau
- (1980) Modern Synthetic Methods , vol.1980 , pp. 91
- Seebach, D.¹ Hungerbühler, E.²

66
- 84985288786
- Dissertation no. 7659, ETH Zürich
- (1984)
- Sutter, M.A.¹

67
- 0022387635
- The systematic name for the macrodiolide building block in this paper is not in accordance with the IUPAC rules
- Liebigs Ann. Chem. , vol.1985 , pp. 2313
- Jackson, R.F.W.¹ Sutter, M.A.² Seebach, D.³

68
- 0009529291
- For a preliminary communication in which most of the work is mentioned which is described here in full detail see
- (1985) J. Am. Chem. Soc. , vol.107 , pp. 5292
- Seebach, D.¹ Chow, H.‐F.² Jackson, R.F.W.³ Lawson, K.⁴ Sutter, M.A.⁵ Thaisrivongs, S.⁶ Zimmermann, J.⁷

69
- 84985201992
- Dissertation no. 6774, ETH Zürich
- (1981)
- Kaiser, H.P.¹

70
- 84985201986
- 47,48.

71
- 37049110577
- J. Chem. Soc., Chem. Commun. , vol.1978 , pp. 976
- Luche, J.L.¹ Gemal, A.L.²

72
- 84985201988
- 3−n + nHCl

73
- 84985194678
- Biological‐chemical methods for attaching or removing the sugars have not yet been tested.

74
- 84985619546
- Doppelte Stereodifferenzierung und eine neue Strategie zur Stereokontrolle in der Organischen Synthese
- (1985) Angewandte Chemie , vol.97 , pp. 1
- Masamune, S.¹ Choy, W.² Petersen, J.S.³ Sita, L.R.⁴

75
- 84985530075
- (1985) Angew. Chem., Int. Ed. Engl. , vol.24 , pp. 1

76
- 84985245243
- Part of the projected Ph. D. thesis of J. Zimmermann, ETH Zürich. Using the same method, products of type 12 – 20 with substituents other than methyl are accessible.

77
- 84985216730
- Liebigs Ann. Chem. , vol.1983 , pp. 2114
- Aebi, J.D.¹ Sutter, M.A.² Wasmuth, D.³ Seebach, D.⁴

78
- 84985223973
- Liebigs Ann. Chem. , vol.1984 , pp. 407
- Aebi, J.D.¹ Sutter, M.A.² Wasmuth, D.³ Seebach, D.⁴

79
- 0001666462
- (1984) Org. Synth. , vol.63 , pp. 109
- Seebach, D.¹ Aebi, J.² Wasmuth, D.³

80
- 0013219285
- (1969) J. Am. Chem. Soc. , vol.91 , pp. 5386
- Su, T.M.¹ Sliwinski, W.F.² Schleyer³

81
- 0000507441
- The b̃‐oxygen effect may be responsible for the fact that using less good leaving groups and solvents other than HMPT gave yields of 20% or less. – It is also conceivable that too good a leaving group or too drastic conditions lead to ionisation of the C–O bond and thus to pinacol‐type rearrangements or hydride shift
- (1969) Carbohyd. Res. , vol.10 , pp. 395
- Richardson, A.C.¹

82
- 84985215035
- Finally, low yields may be due to competing elimination or acetal cleavage. Unpublished results by, (ETH Zürich, respectively).
- (1982)
- Lawson, K.¹ Jakob, R.²

83
- 84985223812
- (1975) J. Org. Chem. , vol.40 , pp. 2141
- Corey, E.J.¹ Crouse, D.N.² Anderson, J.E.³

84
- 0000165260
- For α‐alkylations of b̃‐hydroxy γ‐lactones through alkoxide‐enolates see
- (1981) J. Org. Chem. , vol.46 , pp. 4319
- Shieh, H.M.¹ Prestwich, G.D.²

85
- 0013551093
- (1982) Tetrahedron Lett. , vol.23 , pp. 3055
- Chamberlin, A.R.¹ Dezube, M.²

86
- 0005806942
- (1982) Tetrahedron Lett. , vol.23 , pp. 4643
- Shieh, H.M.¹ Prestwich, G.D.²

87
- 84984270503
- First papers on α‐alkylations of b̃‐hydroxy esters through alkoxide‐enolates
- Tetrahedron Lett. , vol.1973 , pp. 2429
- Herrmann, J.L.¹ Schlessinger, R.H.²

88
- 84984191310
- Tetrahedron Lett. , vol.1977 , pp. 4575
- Kraus, G.A.¹ Taschner, M.J.²

89
- 84943966860
- 2829
- (1979) Helvetica Chimica Acta , vol.62 , pp. 2825
- Fráter, G.¹

90
- 84985053359
- (1980) Helvetica Chimica Acta , vol.63 , pp. 197
- Seebach, D.¹ Wasmuth, D.²

91
- 33845551868
- The protonation of Li‐enolates by diisopropylamine upon addition of electrophiles has recently turned out to be a general phenomenon
- (1983) J. Am. Chem. Soc. , vol.105 , pp. 5390
- Seebach, D.¹ Boes, M.² Naef, R.³ Schweizer, W.B.⁴

92
- 84987564680
- (1985) Helvetica Chimica Acta , vol.68 , pp. 1373
- Laube, Th.¹ Dunitz, J.D.² Seebach, D.³

93
- 84987550840
- (1985) Helvetica Chimica Acta , vol.68 , pp. 1507
- Aebi, J.D.¹ Seebach, D.²

94
- 84984251208
- Tetrahedron Lett. , vol.1973 , pp. 3555
- Hanessian, S.¹ Staub, A.P.A.²

95
- 84985059167
- (1982) Helvetica Chimica Acta , vol.65 , pp. 495
- Seebach, D.¹ Züger, M.²

96
- 48749135623
- (1984) Tetrahedron Lett. , vol.25 , pp. 2747
- Seebach, D.¹ Züger, M.F.²

97
- 0017885064
- (1978) Anal. Chem. , vol.50 , pp. 59
- Quilliam, M.A.¹ Westmore, J.B.²

98
- 29644432244
- (1972) J. Am. Chem. Soc. , vol.94 , pp. 6190
- Corey, E.J.¹ Venkateswarlu, A.²

99
- 37049113544
- J. Chem. Soc., Chem. Commun. , vol.1979 , pp. 156
- Hart, T.W.¹ Metcalfe, D.A.² Scheinmann, F.³

100
- 0000044829
- (1980) J. Am. Chem. Soc. , vol.102 , pp. 2120
- Collum, D.B.¹ McDonald, J.H.² Still, W.C.³

101
- 0000803537
- (1982) Angew. Chem. , vol.94 , pp. 696
- Seebach, D.¹ Prelog, V.²

102
- 84981969973
- (1982) Angew. Chem., Int. Ed. Engl. , vol.21 , pp. 654

103
- 0001222211
- Regio- and stereoselective cross-aldol reactions via dialkylboryl triflates.
- (1980) Bulletin of the Chemical Society of Japan , vol.53 , pp. 174
- Ioue, T.¹ Mukaiyama, T.²

104
- 0012016415
- Stereoselective aldol condensation. Use of chiral boron enolates
- (1981) Journal of the American Chemical Society , vol.103 , pp. 1566
- Masammune, S.¹ Choy, W.² Kerdesky, F.A.J.³ Imperiali, B.⁴

105
- 33845556160
- (1981) J. Am. Chem. Soc. , vol.103 , pp. 3099
- Evans, D.A.¹ Nelson, J.V.² Vogel, E.³ Taber, T.R.⁴

106
- 1542565599
- Springer Verlag, Berlin, Heidelberg, New York
- (1983) Reactivity and Structure Concepts in Organic Chemistry , vol.15
- Kirby, A.J.¹

107
- 0003536850
- Pergamon Press Ltd., Oxford
- (1983) Stereoelectronic Effect in Organic Chemistry
- Deslongchamps, P.¹

108
- 84986364598
- Reversed Stereochemical Course of theMichael Addition of Cyclohexanone to ?-Nitrostyrenes by Using 1-(Trimethylsiloxy)cyclohexene/Dichloro(diisopropoxy)titanium. Preliminary Communication
- (1985) Helvetica Chimica Acta , vol.68 , pp. 319
- Seebach, D.¹ Brook, M.A.²

109
- 84986346889
- (1985) Helvetica Chimica Acta , vol.68 , pp. 162
- Seebach, D.¹ Beck, A.K.² Golińsky, J.³ Hay, J.N.⁴ Laube, Th.⁵

110
- 33845378307
- (1985) J. Am. Chem. Soc. , vol.107 , pp. 3601
- Eyer, M.¹ Seebach, D.²

111
- 0000584420
- Edit, J. D. Morrison, Academic Press, New York
- (1984) Asymmetric Synthesis , vol.3 , pp. 111
- Heathcock, C.H.¹

112
- 0021934568
- (1985) J. Am. Chem. Soc. , vol.107 , pp. 3271
- Ireland, R.E.¹ Häbich, D.² Norbeck, D.W.³

113
- 0021934691
- (1985) J. Am. Chem. Soc. , vol.107 , pp. 3279
- Ireland, R.E.¹ Norbeck, D.W.²

114
- 0022006648
- (1985) J. Am. Chem. Soc. , vol.107 , pp. 3285
- Ireland, R.E.¹ Norbeck, D.W.² Mandel, G.S.³ Mandel, N.S.⁴

115
- 33845377983
- in Organic Synthesis Looking to Molecular Recognition and Design by Stephen
- (1985) Chem. Eng. News , vol.63 , Issue.25 , pp. 26
- Still, W.C.¹ Stinson, C.²

116
- 33947300284
- Our analytical data agree with those in the literature
- (1969) J. Org. Chem. , vol.34 , pp. 2324
- House, H.O.¹ Czuba, L.J.² Gall, M.³ Olmstead, H.D.⁴

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