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Volumn 53, Issue 39, 1997, Pages 13221-13256

Total synthesis of FK-506. Part 1: Construction of the C16-C34 fragment

Author keywords

[No Author keywords available]

Indexed keywords

TACROLIMUS;

EID: 0030828306     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00865-X     Document Type: Article
Times cited : (30)

References (110)
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    • This project was completed in August 1993 and was presented at seminars by REI at Harvard (October, 1993) and by LL at Columbia (October, 1994)
    • (a) This project was completed in August 1993 and was presented at seminars by REI at Harvard (October, 1993) and by LL at Columbia (October, 1994).
  • 2
    • 0342940479 scopus 로고    scopus 로고
    • Taken in part from the PhD Thesis of TDR, University of Virginia, 1991
    • (b) Taken in part from the PhD Thesis of TDR, University of Virginia, 1991.
  • 13
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    • ref. 4(a)
    • (b) ref. 4(a)
  • 14
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    • and references cited therein
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    • Trost, B. M.; Fleming, I. Eds.; Pergamon: New York
    • (d) Roush, W. R. in Comprenhensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds.; Pergamon: New York, 1990; Vol. 2, p1.
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    • Roush, W.R.1
  • 33
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    • It should be pointed out that Stork's ancillary stereocontrol strategy should be applicable in terms of correcting the C24 stereochemistry via, for example, structure i: Stork, G.; Paterson, I.; Lee, F. K. C. J. Am. Chem. Soc. 1982, 104, 4686. (formula presented)
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  • 44
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    • note
    • 3·ether, 50 °C, 78%).
  • 47
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    • 2 was employed to open the epoxide of methyl 2,3-anhydro-5-deoxy-α-L-lyxofuranoside: Fleet, G. W. J.; Shing, T. K. M. Tetrahedron Lett. 1983, 24, 3657.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 3657
    • Fleet, G.W.J.1    Shing, T.K.M.2
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    • Ref. 16
    • (b) Ref. 16.
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    • (c) A similar approach had been reported by Smith and coworkers: Smith, A. B.; Hale, K. J. Tetrahedron Lett. 1989, 30, 1037.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 1037
    • Smith, A.B.1    Hale, K.J.2
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    • Ref. 28(a)
    • (b) Ref. 28(a).
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    • (c) For a review on organocuprate chemistry via transmetallations, see, Wipf, P. Synthesis 1993, 537.
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    • Corey, E.J.1    Boaz, N.W.2
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    • and references cited therein
    • (b) Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277 and references cited therein.
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    • Dess, D.B.1    Martin, J.C.2
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    • Ref. 45
    • (a) Ref. 45.
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    • note
    • 1H NMR spectra of each sample with those of 38 (cf. Scheme 8) indicates that the sample derived from the major isomer possesses the desired α-OH at C26.
  • 90
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    • 3, MeOH, -78 °C
    • 3, MeOH, -78 °C.
  • 91
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    • 3, MeOH-ether, -70 °C; cf. Kishi and coworkers, J. Am. Chem. Soc. 1989, 111, 7525.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 7525
    • Kishi1
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    • 4, THF, -78-0 °C
    • 4, THF, -78-0 °C.
  • 93
    • 0342940415 scopus 로고    scopus 로고
    • DIBALH, PhMe, -78 °0C
    • (d) DIBALH, PhMe, -78 °0C.
  • 94
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    • RedAl, THF or PhMe, rt
    • (e) RedAl, THF or PhMe, rt.
  • 98
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    • LAH, ether, -78 or -100 °C (2:1)
    • Conditions that led to the formation of ≤2:1 β, α-isomer: (i) LAH, ether, -78 or -100 °C (2:1)
  • 100
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    • LAH, LiBr, ether, -78 °C (2:1 plus what seemed to be a 1,3-allylic rearranged product)
    • (k) LAH, LiBr, ether, -78 °C (2:1 plus what seemed to be a 1,3-allylic rearranged product).
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    • The asymmetric catalyst system (S)-α,α-diphenyl-B-butyloxazoborolidine-catecholborane-PhMe did not react with enone 45 (-78 °C to rt), see: (m) Corey, E. J.; Bakshi, R. K. Tetrahedron Lett. 1990, 31, 611.
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    • Corey, E.J.1    Bakshi, R.K.2
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    • Wiley: New York, Chapter 2
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    • Watson, S. C.; Eastham, J. F. J. Organomet. Chem. 1967, 9, 165. For a newer method, see, Winkle, M. R.; Lansinger, J. M.; Ronald, R. C. J. Chem. Soc., Chem. Commun. 1980, 87.
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    • Watson, S.C.1    Eastham, J.F.2


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