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Volumn 53, Issue 22, 1997, Pages 7429-7444

Methylation-ring opening of 3,3-disubstituted 2,3-epoxy alcohols. Synthesis of chiral quaternary fragments for assembly of briaran diterpenes

Author keywords

[No Author keywords available]

Indexed keywords

DITERPENE;

EID: 0030981561     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00453-5     Document Type: Article
Times cited : (25)

References (53)
  • 2
    • 0029107374 scopus 로고
    • and previous articles in this series
    • (b) Faulkner, D. Nat. Prod. Rep. 1995, 12, 223 and previous articles in this series.
    • (1995) Nat. Prod. Rep. , vol.12 , pp. 223
    • Faulkner, D.1
  • 7
    • 4243973410 scopus 로고
    • McMurry, J. E. Chem. Rev. 1989, 89, 1513. For an application of this reaction in the synthesis of ten-membered rings, see: McMurry, J. E.; Siemers, N. O. Tetrahedron Lett. 1994, 35, 4505.
    • (1989) Chem. Rev. , vol.89 , pp. 1513
    • McMurry, J.E.1
  • 8
    • 0028233656 scopus 로고
    • McMurry, J. E. Chem. Rev. 1989, 89, 1513. For an application of this reaction in the synthesis of ten-membered rings, see: McMurry, J. E.; Siemers, N. O. Tetrahedron Lett. 1994, 35, 4505.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 4505
    • McMurry, J.E.1    Siemers, N.O.2
  • 22
    • 0027203724 scopus 로고
    • 3Al-promoted methylation-ring opening of a trisubstituted epoxide at the less substituted position, see: Honda, T.; Tomitsuka, K.; Tsubuki, M. J. Org. Chem. 1993, 58, 4274.
    • (1993) J. Org. Chem. , vol.58 , pp. 4274
    • Honda, T.1    Tomitsuka, K.2    Tsubuki, M.3
  • 29
    • 0012503108 scopus 로고
    • 1,2-Hydride migration in the reaction of disubstituted 2,3-epoxy-1-ols has been shown to occur on treatment with trialkylaluminum reagents when the resultant carbocation species has similar or greater stability than the initial chelated species; see: Honda, M.; Igarashi, T.; Marubayashi, N.; Komori, T. Liebigs Ann. Chem. 1991, 595.
    • (1991) Liebigs Ann. Chem. , pp. 595
    • Honda, M.1    Igarashi, T.2    Marubayashi, N.3    Komori, T.4
  • 34
    • 0342728112 scopus 로고    scopus 로고
    • note
    • 1H-NMR downfield shifts of the hydroxymethyl methylene protons in both isomers; however, only one isomer exhibited a spin-spin coupling of the shifted methylene to the vinyl proton. This isomer was assigned the structure that corresponded to the acetate derived from alcohol 25.
  • 36
    • 0343162729 scopus 로고    scopus 로고
    • note
    • The diastereomeric purities of Mosher ester derivatives were measured using a DNBPG chiral bonded HPLC column (5 micron) available from J. T. Baker Research Products, Phillipsburg, N. J.
  • 42
    • 0343598075 scopus 로고    scopus 로고
    • note
    • Literature precedent suggests the reaction proceeds via anti-opening of the epoxide (references 7-10).
  • 44
    • 0342728094 scopus 로고    scopus 로고
    • note
    • Isolated as a 1:1 mixture of E and Z isomers.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.