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Volumn , Issue 18, 2008, Pages 2821-2822

Formal asymmetric synthesis of (-)-aphanorphine via ring-closing metathesis reaction

Author keywords

Aphanorphine; Asymmetric synthesis; Ring closing metathesis reaction; Tyrosine

Indexed keywords

APHANORPHINE; TYROSINE DERIVATIVE;

EID: 56849119330     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0028-1083498     Document Type: Article
Times cited : (9)

References (36)
  • 3
    • 14644392139 scopus 로고    scopus 로고
    • For a recent review, see
    • For a recent review, see: Zezula, J.; Hudlicky, T. Synlett 2005, 388.
    • (2005) Synlett , pp. 388
    • Zezula, J.1    Hudlicky, T.2
  • 33
    • 0037165329 scopus 로고    scopus 로고
    • For the synthesis of O-Me-D-tyrosine methyl ester hydrochloride salt(4), see: Hulme, A. N.; Rosser, E. M. Org. Lett. 2002, 4, 265.
    • For the synthesis of O-Me-D-tyrosine methyl ester hydrochloride salt(4), see: Hulme, A. N.; Rosser, E. M. Org. Lett. 2002, 4, 265.
  • 36
    • 56849094551 scopus 로고    scopus 로고
    • Compound 8: white solid; mp 136-138°C (Lit.5a 137-138°C, α]D25 -16.9 (c 0.89, CHCl3, Lit.5a [α]D20 -13.4 (c 0.97, CHCl3, Lit.5b [α]D 20 -14.3 (c 0.93, CHCl3, 1H NMR (300 MHz, CDCl3, δ, 1.41 (s, 3 H, 1.41-1.49 (m, 1 H, 1.79 (d, J, 11.1 Hz, 1 H, 2.43 (s, 3 H, 2.91-3.16 (m, 2 H, 3.03 (d, J, 8.4 Hz, 1 H, 3.41 (d, J, 8.7 Hz, 1 H, 3.80 (s, 3 H, 4.40 (t, J, 3.3 Hz, 1 H, 6.74 (dd, J, 8.4, 2.4 Hz, 1 H, 6.79 (d, J, 2.7 Hz, 1 H, 6.99 (d, J, 8.1 Hz, 1 H, 7.30 (d, J, 8.1 Hz, 2 H, 7.71 (d, J, 8.1 Hz, 2 H, 13C NMR 75.47 MHz, CDCl3, δ, 20.8, 21.6, 38.3, 41.8, 42.4, 55.4, 58.0, 63.1, 110.3, 111.9, 125.5, 127.3, 129.8, 130.6, 135.9, 143.4, 145.1, 158.2. ESI-MS: m/z
    • 3S + Na: 380.1296; found: 380.1308.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.