메뉴 건너뛰기




Volumn 41, Issue 17, 1985, Pages 3479-3495

Intramolecular cycloaddition reactions of exocyclic nitrones. Application in the total synthesis of terpenes

Author keywords

[No Author keywords available]

Indexed keywords


EID: 38949213484     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(01)96702-X     Document Type: Article
Times cited : (46)

References (88)
  • 3
    • 84980167410 scopus 로고
    • For reviews of this intramolecular cycloaddition reaction see, Int. Ed. Engl.
    • (1977) Angew. Chem. , vol.16 , pp. 10
    • Oppolzer1
  • 5
    • 84989463058 scopus 로고
    • 1,3-Dipolar Cycloaddition Reactions of Nitrones
    • For reviews of this intramolecular cycloaddition reaction
    • (1975) Synthesis , pp. 205
    • Black1    Crozier2    Davis3
  • 15
    • 0000650546 scopus 로고
    • α-Bisabolol
    • The preparation of monocyclic terpenes by implementation of this general strategy has been reported.
    • (1979) J. Org. Chem. , vol.44 , pp. 953
    • Schwartz1    Swanson2
  • 17
    • 84984276334 scopus 로고
    • iridoids
    • The preparation of monocyclic terpenes by implementation of this general strategy has been reported., The preparation of the perhydroazulene skeleton has also been accomplished.
    • (1983) Bull. Soc. Chim. Belg. , vol.92 , pp. 1019
    • Vandewalle1    Storme2    Callant3
  • 25
    • 84918088304 scopus 로고    scopus 로고
    • a For a recent compilation of: previous hirsutene total syntheses, see ref. 3 of ref. 6b
  • 31
    • 84918088303 scopus 로고    scopus 로고
    • This structural assignment is based on very similar coupling constants and chemical shift values of the oxymethylene proton resonances for 21 and 14 in contrast to those for 26.
  • 40
    • 0001223301 scopus 로고
    • In our hands, the Wolf-Kishner reduction of endo-3-oxobicyclo[3.2.1]octane-6-carboxylic acid proceeded with partial (80%) concomitant epimerization to the exo-acid.
    • (1979) J. Org. Chem. , vol.44 , pp. 2210
    • Moriarty1    Chien2    Adams3
  • 43
    • 84918087319 scopus 로고    scopus 로고
    • For a partial listing, see ref. 2 in ref. 6a.
  • 44
    • 0346701595 scopus 로고
    • Die synchrone Fragmentierung von ?-Amino-cycloalkylhalogeniden 1. Teil. Die Solvolyse von 1-Amino-3-brom-adamantanen. Fragmentierungs-Reaktionen. 10. Mitteilung
    • To the best of our knowledge, only adamantane derivatives have been investigated, for example, 1-amino-3-chloro-adamantane
    • (1964) Helvetica Chimica Acta , vol.47 , pp. 1870
    • Grob1    Schwarz2
  • 52
    • 33847088517 scopus 로고
    • The stereochemistry of the Sakurai reaction with substituted cyclohexenones and cycloheptenones has recently been reported.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 1673
    • Hosomi1    Sakurai2
  • 55
    • 0343121320 scopus 로고
    • The reductive cleavage of γ-bromo ketones has been observed previously. See
    • (1968) Tetrahedron , vol.24 , pp. 1655
    • Baker1    Davis2
  • 56
    • 0013584673 scopus 로고
    • A Stereoselective Approach to the Spiro [4, 5]decane System via Intramolecular Photocycloaddition and Reductive Fragmentation. Preliminary communication
    • The reductive cleavage of γ-bromo ketones has been observed previously. See
    • (1981) Helvetica Chimica Acta , vol.64 , pp. 186
    • Oppolzer1    Gorrichon2    Bird3
  • 58
    • 84918087317 scopus 로고    scopus 로고
    • Commercially available from Petrarch Systems, Inc.
  • 59
    • 5244340618 scopus 로고
    • Similar isomerizations have been observed previously and attributed to the angle strain inherent in bicyclo[3.3.0]oct-1-ene, see
    • (1975) J. Org. Chem. , vol.40 , pp. 1699
    • Agosta1    Wolff2
  • 77
    • 84918087315 scopus 로고    scopus 로고
    • 26a
  • 78
    • 84918087314 scopus 로고    scopus 로고
    • Prepared in 20% yield by addition of 2-propenylmagnesium bromide to the sodium enolate (NaH) of 1,3-cyclo- hexandione followed by standard aqueous workup.
  • 79
    • 84918087313 scopus 로고    scopus 로고
    • 47b to the sodium enolate (NaH) of 1,3-cyclohexandione
  • 83
    • 84918087311 scopus 로고    scopus 로고
    • 2; (4) PCC.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.