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Volumn 118, Issue 44, 1996, Pages 10926-10927

Enantioselective total synthesis of antifungal agent Sch 38516

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFUNGAL AGENT; SCH 38516; UNCLASSIFIED DRUG;

EID: 0029846989     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9626603     Document Type: Article
Times cited : (101)

References (39)
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    • Diastereoselective carbomagnesation: (a) Hoveyda, A. H.; Xu, Z. J. Am. Chem. Soc. 1991, 113, 5079-5080. (b) Houri, A. F.; Didiuk, M. T.; Xu, Z.; Horan, N. R.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6614-6624. Enantioselective carbomagnesation: (c) Morken, J. P.; Didiuk, M. T.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6697-6698. (d) Visser, M. S.; Heron, N. M.; Didiuk, M. T.; Sagal, J. F.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 4291-4298.
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    • Diastereoselective carbomagnesation: (a) Hoveyda, A. H.; Xu, Z. J. Am. Chem. Soc. 1991, 113, 5079-5080. (b) Houri, A. F.; Didiuk, M. T.; Xu, Z.; Horan, N. R.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6614-6624. Enantioselective carbomagnesation: (c) Morken, J. P.; Didiuk, M. T.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6697-6698. (d) Visser, M. S.; Heron, N. M.; Didiuk, M. T.; Sagal, J. F.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 4291-4298.
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    • note
    • At this point, the diastereomer derived from minor dihydroxylation enantiomer is separated from 3b.
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    • note
    • This experiment was carried out by Mr. Daniel La of these laboratories.
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    • Pozsgay, V. J. Am. Chem. Soc. 1995, 117, 6673-6681. Although the secondary amine of the unmasked carbohydrate (product of hydrogenation) could be protected, attempts to acylate the two secondary carbinols and the hemiacetal hydroxyl group, under a variety of conditions, led to the formation of complex mixtures of products.
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    • For other macrocyclic ring syntheses through catalytic ring closing metathesis, see: (a) Martin, S. F.; Liao, Y.; Wong, Y.; Rein, T. Tetrahedron Lett. 1994, 35, 691-694. (b) Borer, B. C.; Deerenberg, S.; Bieraugel, H.; Pandit, U. K. Tetrahedron Lett. 1994, 35, 3191-3194. (c) Martin, S. F.; Liao, Y.; Chen, H.-J.; Patzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 35, 6005-6008. (d) Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855-5856. (e) Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364-12365. (f) Furstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942-3943. (g) McKervey, M. A.; Pitarch, M. J. Chem. Soc., Chem. Commun. 1996, 1689-1690.
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    • For other macrocyclic ring syntheses through catalytic ring closing metathesis, see: (a) Martin, S. F.; Liao, Y.; Wong, Y.; Rein, T. Tetrahedron Lett. 1994, 35, 691-694. (b) Borer, B. C.; Deerenberg, S.; Bieraugel, H.; Pandit, U. K. Tetrahedron Lett. 1994, 35, 3191-3194. (c) Martin, S. F.; Liao, Y.; Chen, H.-J.; Patzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 35, 6005-6008. (d) Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855-5856. (e) Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364-12365. (f) Furstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942-3943. (g) McKervey, M. A.; Pitarch, M. J. Chem. Soc., Chem. Commun. 1996, 1689-1690.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 3191-3194
    • Borer, B.C.1    Deerenberg, S.2    Bieraugel, H.3    Pandit, U.K.4
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    • For other macrocyclic ring syntheses through catalytic ring closing metathesis, see: (a) Martin, S. F.; Liao, Y.; Wong, Y.; Rein, T. Tetrahedron Lett. 1994, 35, 691-694. (b) Borer, B. C.; Deerenberg, S.; Bieraugel, H.; Pandit, U. K. Tetrahedron Lett. 1994, 35, 3191-3194. (c) Martin, S. F.; Liao, Y.; Chen, H.-J.; Patzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 35, 6005-6008. (d) Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855-5856. (e) Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364-12365. (f) Furstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942-3943. (g) McKervey, M. A.; Pitarch, M. J. Chem. Soc., Chem. Commun. 1996, 1689-1690.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 6005-6008
    • Martin, S.F.1    Liao, Y.2    Chen, H.-J.3    Patzel, M.4    Ramser, M.N.5
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    • For other macrocyclic ring syntheses through catalytic ring closing metathesis, see: (a) Martin, S. F.; Liao, Y.; Wong, Y.; Rein, T. Tetrahedron Lett. 1994, 35, 691-694. (b) Borer, B. C.; Deerenberg, S.; Bieraugel, H.; Pandit, U. K. Tetrahedron Lett. 1994, 35, 3191-3194. (c) Martin, S. F.; Liao, Y.; Chen, H.-J.; Patzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 35, 6005-6008. (d) Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855-5856. (e) Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364-12365. (f) Furstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942-3943. (g) McKervey, M. A.; Pitarch, M. J. Chem. Soc., Chem. Commun. 1996, 1689-1690.
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    • Miller, S.J.1    Grubbs, R.H.2
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    • For other macrocyclic ring syntheses through catalytic ring closing metathesis, see: (a) Martin, S. F.; Liao, Y.; Wong, Y.; Rein, T. Tetrahedron Lett. 1994, 35, 691-694. (b) Borer, B. C.; Deerenberg, S.; Bieraugel, H.; Pandit, U. K. Tetrahedron Lett. 1994, 35, 3191-3194. (c) Martin, S. F.; Liao, Y.; Chen, H.-J.; Patzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 35, 6005-6008. (d) Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855-5856. (e) Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364-12365. (f) Furstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942-3943. (g) McKervey, M. A.; Pitarch, M. J. Chem. Soc., Chem. Commun. 1996, 1689-1690.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 12364-12365
    • Clark, T.D.1    Ghadiri, M.R.2
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    • For other macrocyclic ring syntheses through catalytic ring closing metathesis, see: (a) Martin, S. F.; Liao, Y.; Wong, Y.; Rein, T. Tetrahedron Lett. 1994, 35, 691-694. (b) Borer, B. C.; Deerenberg, S.; Bieraugel, H.; Pandit, U. K. Tetrahedron Lett. 1994, 35, 3191-3194. (c) Martin, S. F.; Liao, Y.; Chen, H.-J.; Patzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 35, 6005-6008. (d) Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855-5856. (e) Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364-12365. (f) Furstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942-3943. (g) McKervey, M. A.; Pitarch, M. J. Chem. Soc., Chem. Commun. 1996, 1689-1690.
    • (1996) J. Org. Chem. , vol.61 , pp. 3942-3943
    • Furstner, A.1    Langemann, K.2
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    • For other macrocyclic ring syntheses through catalytic ring closing metathesis, see: (a) Martin, S. F.; Liao, Y.; Wong, Y.; Rein, T. Tetrahedron Lett. 1994, 35, 691-694. (b) Borer, B. C.; Deerenberg, S.; Bieraugel, H.; Pandit, U. K. Tetrahedron Lett. 1994, 35, 3191-3194. (c) Martin, S. F.; Liao, Y.; Chen, H.-J.; Patzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 35, 6005-6008. (d) Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855-5856. (e) Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364-12365. (f) Furstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942-3943. (g) McKervey, M. A.; Pitarch, M. J. Chem. Soc., Chem. Commun. 1996, 1689-1690.
    • (1996) J. Chem. Soc., Chem. Commun. , pp. 1689-1690
    • McKervey, M.A.1    Pitarch, M.2
  • 39
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    • Efforts to prepare more soluble derivatives of the macrolactam alcohol (e.g., the derived TMS ether) which would also be suitable for glycosylation by other methods (e.g., involving triacetate 7) were not successful. For an example, see: Mukaiyama, T.; Katsurada, M.; Takashima, T. Chem. Lett. 1991, 985-988.
    • (1991) Chem. Lett. , pp. 985-988
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