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Volumn 71, Issue 14, 2006, Pages 5369-5372

An efficient, stereoselective synthesis of the hydroxyethylene dipeptide isostere core for the HIV protease inhibitor A-792611

Author keywords

[No Author keywords available]

Indexed keywords

DIASTEREOMERICALLY; HOFMANN REARRANGEMENTS; KINETIC PROTONATION; LACTONE;

EID: 33745728268     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060737s     Document Type: Article
Times cited : (10)

References (25)
  • 6
    • 33745694598 scopus 로고    scopus 로고
    • note
    • Samples of each diastereomer were isolated by flash column chromatography and the relative stereochemistry was assigned by 2D NMR experiments: see the Supporting Information for details.
  • 7
    • 11444264816 scopus 로고    scopus 로고
    • For alternate diastereoselective routes to α/γ-substituted lactones, see: (a) Haug, B. E.; Rich, D. H. Org. Lett. 2004, 6, 4783-4786.
    • (2004) Org. Lett. , vol.6 , pp. 4783-4786
    • Haug, B.E.1    Rich, D.H.2
  • 17
    • 0001302486 scopus 로고
    • For a discussion of stereoselective kintetic protonation of enolates, see: (a) Zimmerman, H. E. Acc. Chem. Res. 1987, 20, 263-268.
    • (1987) Acc. Chem. Res. , vol.20 , pp. 263-268
    • Zimmerman, H.E.1
  • 22
    • 33745722818 scopus 로고    scopus 로고
    • note
    • 6 at 107 °C. Boc-peaks coalesced to two sharp peaks at 0.93 and 0.91 ppm.
  • 23
    • 33745722819 scopus 로고    scopus 로고
    • note
    • Amide 10 slowly converts back to lactone 5 in protic solvents such as methanol but is stable in the solid form and in aprotic solvents. The ammonolysis reaction was run in DME to afford 10 as a slurry without an increase in reaction time.
  • 25
    • 33745694597 scopus 로고    scopus 로고
    • note
    • The scope and mechanism of the use of N,N-dibromo-5,5-dimethylhydantoin for Hofmann reactions is under investigation.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.