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Volumn 14, Issue 22, 2008, Pages 6606-6608

Diastereoselective total synthesis of (±)-codeine

Author keywords

Alkaloids; Diastereoselectivity; Heck reaction; Hydroamination; Rearrangement; Total synthesis

Indexed keywords

AMINES; ORGANIC COMPOUNDS;

EID: 53849091312     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200800744     Document Type: Article
Times cited : (47)

References (32)
  • 4
    • 27144524460 scopus 로고    scopus 로고
    • For the syntheses of morphine and codeine after ref. [Ic] see: a B. M. Trost, W. Tang, F. D. Toste, J. Am. Chem. Soc. 2005, 127, 14785-14803
    • For the syntheses of morphine and codeine after ref. [Ic] see: a) B. M. Trost, W. Tang, F. D. Toste, J. Am. Chem. Soc. 2005, 127, 14785-14803
  • 13
    • 0035905367 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2001, 40, 4745-4746
    • (2001) Angew. Chem. Int. Ed , vol.40 , pp. 4745-4746
  • 18
    • 53849083859 scopus 로고    scopus 로고
    • Acid 10 was obtained by Birch reduction of p-methoxyphenyl acetic acid followed by protection with ethylene glycol (See Supporting Information).
    • Acid 10 was obtained by Birch reduction of p-methoxyphenyl acetic acid followed by protection with ethylene glycol (See Supporting Information).
  • 19
    • 0034730654 scopus 로고    scopus 로고
    • For an example of reduction of the reaction time (19.5 h to 5 h) of a Heck arylation reaction under ligand-free conditions see: M. Qadir, T. Möchel, K. K. Hii, Tetrahedron 2000, 56, 7975-7979.
    • For an example of reduction of the reaction time (19.5 h to 5 h) of a Heck arylation reaction under ligand-free conditions see: M. Qadir, T. Möchel, K. K. Hii, Tetrahedron 2000, 56, 7975-7979.
  • 29
    • 53849113037 scopus 로고    scopus 로고
    • Variations of reaction time, temperature, or use of microwaves did not modify the amount of diene produced
    • Variations of reaction time, temperature, or use of microwaves did not modify the amount of diene produced.
  • 32
    • 0037069730 scopus 로고    scopus 로고
    • [2b]
    • [2b]


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.