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Volumn 45, Issue 11, 2004, Pages 2289-2292

Vitamin D: A concise synthesis of the C19 hydroxylated enyne A-ring, an interesting precursor for the preparation of C19 substituted vitamin D analogues

Author keywords

Criegee rearrangement; Epoxide ring opening; Limonene; Vitamin D

Indexed keywords

1,2 LIMONENE OXIDE; ALKYNE DERIVATIVE; EPOXIDE; ETHYLENE OXIDE; LIMONENE; LITHIUM ACETYLIDE; UNCLASSIFIED DRUG; VITAMIN D DERIVATIVE;

EID: 1242338136     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.01.121     Document Type: Article
Times cited : (9)

References (29)
  • 14
    • 33751392466 scopus 로고
    • Epoxidation of (-)-(S)-limonene by m-CPBA gave a 3:2 trans/cis mixture of 1,2-limonene oxide in 80% yield. The ratio was determined by GC analysis and confirmed by Cane and Coates:
    • Epoxidation of (-)-(S)-limonene by m-CPBA gave a 3:2 trans/cis mixture of 1,2-limonene oxide in 80% yield. The ratio was determined by GC analysis and confirmed by Cane and Coates: Cane D.E., Yang G., Coates R.M., Pyun H.-J., Hohn T.M. J. Org. Chem. 57:1992;3454-3462.
    • (1992) J. Org. Chem. , vol.57 , pp. 3454-3462
    • Cane, D.E.1    Yang, G.2    Coates, R.M.3    Pyun, H.-J.4    Hohn, T.M.5
  • 19
    • 0000918192 scopus 로고
    • The relative configuration of each diastereoisomers was assigned by comparison with the spectrum of the cis- and trans-4-hydroxy-methylcyclohexene oxides reported in the literature, and also the integration of each signal:
    • The relative configuration of each diastereoisomers was assigned by comparison with the spectrum of the cis- and trans-4-hydroxy-methylcyclohexene oxides reported in the literature, and also the integration of each signal: Delay D., Ohloff G. Helv. Chim. Acta. 62:1979;2168-2173.
    • (1979) Helv. Chim. Acta , vol.62 , pp. 2168-2173
    • Delay, D.1    Ohloff, G.2
  • 20
    • 85030895051 scopus 로고    scopus 로고
    • The stereochemistry was supported by NOESY experiments, that showed correlation between propargylic H-2 and methyl-1 in compound 10a , but not between H-2 and H-4.
  • 21
    • 1242266399 scopus 로고
    • In a pioneer work, Inhoffen reported that the addition of lithium acetylide to 4-(tetrahydropyran-2-yloxy)-methylcyclohexene oxide proceeds in just 33% yield. No explanation of the origin of this low yield and no structure of side products were proposed:
    • In a pioneer work, Inhoffen reported that the addition of lithium acetylide to 4-(tetrahydropyran-2-yloxy)-methylcyclohexene oxide proceeds in just 33% yield. No explanation of the origin of this low yield and no structure of side products were proposed: Inhoffen H.H., Weissemerel K., Quinkert G., Bartling D. Chem. Ber. 89:1956;853-861.
    • (1956) Chem. Ber. , vol.89 , pp. 853-861
    • Inhoffen, H.H.1    Weissemerel, K.2    Quinkert, G.3    Bartling, D.4
  • 22
    • 85040807459 scopus 로고
    • For other studies on ring opening of methylcyclohexene oxide by lithium acetylide, see:
    • For other studies on ring opening of methylcyclohexene oxide by lithium acetylide, see: Hanack M., Kunzmann E., Schumacher W. Synthesis. 1978;26-27.
    • (1978) Synthesis , pp. 26-27
    • Hanack, M.1    Kunzmann, E.2    Schumacher, W.3
  • 24
    • 0035920616 scopus 로고    scopus 로고
    • Various examples reported in the literature showed that nucleophilic attacks of cis- and trans-4-substituted methylcyclohexene oxides initiate the selective ring opening of trans isomers, exclusively. For recent references, with nitrogen centred nucleophiles: with phosphorus centred nucleophiles:
    • Various examples reported in the literature showed that nucleophilic attacks of cis- and trans-4-substituted methylcyclohexene oxides initiate the selective ring opening of trans isomers, exclusively. For recent references, with nitrogen centred nucleophiles: Chrisman W., Camara J.N., Marcellini K., Singaram B., Goralski C.T., Hasha D.L., Rudolf P.R., Nicholson L.W., Borodychuk K.K. Tetrahedron Lett. 42:2001;5805-5807. with phosphorus centred nucleophiles:
    • (2001) Tetrahedron Lett. , vol.42 , pp. 5805-5807
    • Chrisman, W.1    Camara, J.N.2    Marcellini, K.3    Singaram, B.4    Goralski, C.T.5    Hasha, D.L.6    Rudolf, P.R.7    Nicholson, L.W.8    Borodychuk, K.K.9
  • 29
    • 85030899771 scopus 로고    scopus 로고
    • note
    • +], 45), 151 (40), 136 (19), 123 (16), 109 (100), 91 (49), 81 (21), 79 (24), 77 (20), 65 (21), 43 (11).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.