Total synthesis of FK-506. Part 2: Completion of the synthesis

Tetrahedron

Volumn 53, Issue 39, 1997, Pages 13257-13284

  Ireland, Robert E ^a   Liu, Longbin ^a,b   Roper, Thomas D ^a   Gleason, James L ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

^b AMGEN INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TACROLIMUS;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030750871     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00866-1     Document Type: Article

References (54)

1. (i) For part 1, see the preceding paper. (ii) (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). Taken in part from PhD Theses of (b) TDR (1991) and (c) JLG (1994), University of Virginia.
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8. The unstable aldehyde 7 was prepared by Dess-Martin oxidation (85%) of the corresponding alcohol 3b immediately before use. Ireland, R. E.; Highsmith, T. K.; Gegnas, L. D.; Gleason, J. L. J. Org. Chem. 1992, 57, 5071.
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11. For related reductions using this protocol, see: (b) Ref. 4.
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17. We thank Dr. Robert S. Meissner for making this provocative and fortunate suggestion.
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36. When this new compound was subjected to the β-elimination condition, it was converted to the desired enediol ketal in ∼20% yield. The remainging mass balance was either starting materials or decomposition product.
37. 2 were used with LiHMDS (80 equiv), the reaction became very slow.
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39. Both epi-23 and 23 have identical spectroscopic data, and optical rotations (-12.5° and -13.7°) within instrumental errors, see experimental part
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50. In contrast, oxidations of noncyclic enediol ethers were not as efficient: (a) White, J. D.; Jeffrey, S. C. J. Org. Chem. 1996, 61, 2600.
51. (b) Ref. 7(c).
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53. 2 upon mixing with MeMgBr.
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