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Volumn 122, Issue 36, 2000, Pages 8654-8664

Evolution of a gram-scale synthesis of (+)-discodermolide

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ANTIMITOTIC AGENT; DISCODERMOLIDE; PHOSPHONIUM DERIVATIVE;

EID: 0034644383     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0015287     Document Type: Review
Times cited : (257)

References (117)
  • 5
    • 33847550816 scopus 로고    scopus 로고
    • The mode of action involves blocking the S phase of the cell cycle see ref 2.
    • The mode of action involves blocking the S phase of the cell cycle see ref 2.
  • 34
    • 0342826602 scopus 로고    scopus 로고
    • Ph.D. Thesis, Harvard University, Cambridge, MA
    • (f) Halstead, D. P. Ph.D. Thesis, Harvard University, Cambridge, MA, 1998.
    • (1998)
    • Halstead, D.P.1
  • 56
    • 33847552787 scopus 로고    scopus 로고
    • Complete crystallographic data for 12, 13, 15, 49, 89, and 1 have been deposited in the Cambridge Crystallographic Data Centre.
    • Complete crystallographic data for 12, 13, 15, 49, 89, and 1 have been deposited in the Cambridge Crystallographic Data Centre.
  • 60
    • 33847560817 scopus 로고    scopus 로고
    • Alcohol 17 could also be converted to iodide A in 94% overall yield via tosylation (TsCl, pyridine) followed by displacement with sodium iodide in DMF.
    • Alcohol 17 could also be converted to iodide A in 94% overall yield via tosylation (TsCl, pyridine) followed by displacement with sodium iodide in DMF.
  • 61
    • 33847571572 scopus 로고    scopus 로고
    • We also explored the use of the norephedrine-derived oxazolidinone 11 employed in the synthesis of CP. Unfortunately the corresponding aldol product was obtained as an oil. In addition, reductive removal of the auxiliary resulted in competitive opening of the oxazolidinone ring; thus, oxazolidinone 9 was the auxiliary of choice for the construction of fragment A.
    • We also explored the use of the norephedrine-derived oxazolidinone 11 employed in the synthesis of CP. Unfortunately the corresponding aldol product was obtained as an oil. In addition, reductive removal of the auxiliary resulted in competitive opening of the oxazolidinone ring; thus, oxazolidinone 9 was the auxiliary of choice for the construction of fragment A.
  • 64
    • 0142005963 scopus 로고    scopus 로고
    • For leading references on silicon migration from oxygen to carbon, see: (a) Jung, M. E.; Nichols, C. J. J. Org. Chem. 1996, 61, 9065.
    • (1996) J. Org. Chem. , vol.61 , pp. 9065
    • Jung, M.E.1    Nichols, C.J.2
  • 71
    • 33847558321 scopus 로고    scopus 로고
    • 3Al].
    • 3Al].
  • 73
    • 33847090277 scopus 로고
    • Thesis, University of Pennsylvania, Philadelphia, PA, 1997. Evans, D. A.; Truesdale, L. K.; Grimm, K. G.; Nesbitt, S. L.
    • 2; see: Qui, Y. Ph.D. Thesis, University of Pennsylvania, Philadelphia, PA, 1997. Evans, D. A.; Truesdale, L. K.; Grimm, K. G.; Nesbitt, S. L. J. Am. Cliem. Soc. 1977, 99, 5009.
    • (1977) J. Am. Cliem. Soc. , vol.99 , pp. 5009
    • Ph.d, Q.Y.1
  • 76
    • 33847546667 scopus 로고    scopus 로고
    • See ref 32, Chapter 11.
    • See ref 32, Chapter 11.
  • 77
    • 33847567900 scopus 로고    scopus 로고
    • Selected NOE values (%) and 'H NMR coupling constants for 36 and 39. We thank Dr. Peter Dormer for technical assistance. matrix equation presented
    • Selected NOE values (%) and 'H NMR coupling constants for 36 and 39. We thank Dr. Peter Dormer for technical assistance. matrix equation presented
  • 80
    • 0001043464 scopus 로고
    • (b) Negishi, E.; Swanson, D. R.; Roussel, C. / Org. Chem. 1990,55,5406.
    • (a) Bailey, W. F.; Punzalan, E. R. J. Org. Chem. 1990, 55, 5404. (b) Negishi, E.; Swanson, D. R.; Roussel, C. / Org. Chem. 1990,55,5406.
    • (1990) Org. Chem. , vol.55 , pp. 5404
    • Bailey, W.F.1    Punzalan, E.R.J.2
  • 83
    • 0000908260 scopus 로고    scopus 로고
    • While attempting to optimize the formation of 46 via the Zhao protocol, we observed significant formation of methyl ketone and epoxide byproducts. These results suggest that formation of an epoxyphosphonium salt is competitive with Wittig olefination. A detailed discussion of the Zhao chemistry has been published and will not be repeated here; see: Arimoto, H.; Kaufman, M. D.; Kobayashi, K.; Qui, Y.; Smith, A. B., III. Synlett 1998, 765.
    • (1998) Synlett , pp. 765
    • Arimoto, H.1    Kaufman, M.D.2    Kobayashi, K.3    Qui, Y.4    Smith, A.B.5
  • 84
    • 33847556361 scopus 로고    scopus 로고
    • In the Marshall synthesis of 1, a Suzuki coupling strategy was employed requiring 2 equiv of the alkyl iodide; see ref lid.
    • In the Marshall synthesis of 1, a Suzuki coupling strategy was employed requiring 2 equiv of the alkyl iodide; see ref lid.
  • 89
    • 33847566530 scopus 로고    scopus 로고
    • note
    • rel = 0-5.48 kJ/mol) were judged suitably disposed to facilitate displacement of the iodide by the olefin. Of these conformers, the average distance between C(I) and C(5) was only 3.05 Å (SD = 0.02 Å) while the average I-C(1)-C(5) angle was 161.2° (SD = 0.4°).
  • 91
    • 0000345933 scopus 로고
    • For reviews on the use of high pressure in organic synthesis, see: (a) Organic Synthesis at High Pressure; Matsumoto, K., Morrin Acheson, R., Eds.; John Wiley: New York, 1991.
    • Dauben, W. G.; Gerdes, J. M.; Bunce, R. A. J. Org. Chem. 1984, 49,4293. For reviews on the use of high pressure in organic synthesis, see: (a) Organic Synthesis at High Pressure; Matsumoto, K., Morrin Acheson, R., Eds.; John Wiley: New York, 1991.
    • (1984) J. Org. Chem. , vol.49 , pp. 4293
    • Dauben, W.G.1    Gerdes, J.M.2    Bunce, R.A.3
  • 96
    • 33847539437 scopus 로고    scopus 로고
    • Heathcock has also utilized the Yamamoto protocol; see ref lOb.
    • Heathcock has also utilized the Yamamoto protocol; see ref lOb.
  • 99
    • 33847552575 scopus 로고    scopus 로고
    • note
    • We thank Professor Schreiber (Harvard University) for providing a sample of synthetic (-)-discodermolide.
  • 100
    • 33847546439 scopus 로고
    • Helmchen, G., Hoffman, R. W., Mulzer, J., Schaumann, Eds.; Thieme Verlag: New York, Vol. E21b, Chapter
    • For a general discussion of nucleophilic additions to α-chiral carbonyl compounds, see: Devant, R. M.; Radunz, H.-E. In Methods of Organic Chemistry; Helmchen, G., Hoffman, R. W., Mulzer, J., Schaumann, Eds.; Thieme Verlag: New York, 1995; Vol. E21b, Chapter 1.3.
    • (1995) Methods of Organic Chemistry , pp. 13
    • Devant, R.M.1    Radunz, H.-E.2
  • 101
    • 33847561040 scopus 로고    scopus 로고
    • Paterson reported the synthesis of the enantiomer of 71; see ref 10a. However, use as a substrate for Wittig olefination was not reported.
    • Paterson reported the synthesis of the enantiomer of 71; see ref 10a. However, use as a substrate for Wittig olefination was not reported.
  • 103
    • 33847541976 scopus 로고    scopus 로고
    • 2,3 = 9.8 Hz.
    • 2,3 = 9.8 Hz.
  • 104
    • 33847547356 scopus 로고    scopus 로고
    • The BPS ether aldehyde 79, a substrate lacking the Weinreb amide moiety furnished the Felkin addition product 80 over the anti-Felkin adduct 81 (3:1): matrix equation presented
    • The BPS ether aldehyde 79, a substrate lacking the Weinreb amide moiety furnished the Felkin addition product 80 over the anti-Felkin adduct 81 (3:1): matrix equation presented
  • 105
    • 0001091444 scopus 로고
    • For a discussion of chelation-controlled carbonyl additions see: Reetz, M. T. Ace. Chem. Res. 1993, 26, 462.
    • (1993) Ace. Chem. Res. , vol.26 , pp. 462
    • Reetz, M.T.1
  • 106
    • 0342371555 scopus 로고
    • 13C NMR data strongly supports coordination of Sn(IV) with the carbonyls of 82. (a) Santelli-Rouvier, C. Tetrahedron Lett. 1984, 25, 4371.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 4371
    • Santelli-Rouvier, C.1
  • 110
    • 33847565710 scopus 로고    scopus 로고
    • note
    • 3H again afforded only a 3: 1 mixture of diols. matrix equation presented
  • 111
    • 33847569342 scopus 로고    scopus 로고
    • Minor amounts of elimination products 91 and 92 were also observed. matrix equation presented
    • Minor amounts of elimination products 91 and 92 were also observed. matrix equation presented
  • 112
    • 33847568519 scopus 로고    scopus 로고
    • note
    • Both Myles and Paterson employed a two-step diene synthesis in their syntheses of discodermolide. In our hands this route did successfully deliver discodermolide in 31 total steps (22 in the longest linear sequence); however, due to the capricious yields observed, this approach was not conducive to large-scale synthesis.
  • 113
    • 33847569808 scopus 로고    scopus 로고
    • All attempts to remove selectively the primary PMB ether in the presence of the secondary PMB ether proved unsuccessful.
    • All attempts to remove selectively the primary PMB ether in the presence of the secondary PMB ether proved unsuccessful.
  • 117
    • 33847563950 scopus 로고    scopus 로고
    • We thank Novartis for informing us that discodermolide is stable in acetonitrile.
    • We thank Novartis for informing us that discodermolide is stable in acetonitrile.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.